1H-indazole-7-carboxylic acid

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Warning

• 유해·위험 문구

  H315：피부에 자극을 일으킴

  H319：눈에 심한 자극을 일으킴

  H335：호흡 자극성을 일으킬 수 있음

• 예방조치문구

  P261：분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.

  P304+P340：흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.

  P305+P351+P338：눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

  P405：밀봉하여 저장하시오.

1H-indazole-7-carboxylic acid 화학적 특성, 용도, 생산

• 용도

  1H-indazole-7-carboxylic Acid is an inhibitor of nitric oxide synthases.

• 제조 방법

  Synthesis of 1H-indazole-7-carboxylic acid, H2L4: To 60 mL anhydrous toluene under a nitrogen atmosphere was added methyl-2-amino-3-methylbenzoate (1.8 g, 11 mmol) and KOAc (560 mg, 5.7 mmol), and the mixture heated to reflux, at which time acetic anhydride (3.2 mL, 34 mmol) was added and the mixture stirred at reflux for 10 min. Isoamyl nitrite (2.3 mL, 18 mmol) was added over 30 min and the mixture refluxed overnight. On cooling, the mixture was filtered and evaporated to dryness to give 1.6 g of a pale brown solid, which analysed for methyl 1H-indazole-7-carboxylate. This material was taken up in 40 mL THF, added to a solution of LiOH (5 g, 210 mmol) in 40 mL water, and heated at reflux for 48 h. On cooling, the mixture was concentrated on a rotary evaporator and the resulting aqueous phase filtered and adjusted to pH 4 with dilute HCl, to precipitate the product, which was filtered, washed with water and dried under vacuum. Yield 810 mg, 45%; mp 218–222 °C (decomp);
  δH (500 MHz, d6-DMSO): 7.23 (t, 1H, J = 7.5 Hz, H4 ), 7.97 (dd, 1H, J = 7.5, 1.0 Hz, H3 ), 8.06 (dd, 1H, J = 7.8, 0.8 Hz, H5 ), 8.21 (s, 1H, H2 ), 13.1 (br s, 2H, H1 & H6 ); δc (125 MHz, d6-DMSO): 113.7, 120.1, 124.6, 126.5, 129.0, 134.3, 138.0, 167.0; HRMS-ESI m/z: found: 163.0503; C8H7N2O2 requires: 163.0502 [M + H+ ]; ˉνmax/cm?1 (KBr): 3316 s br, 1700 s, 1619 m, 1592 m, 1509 m, 1285 s, 1201 m, 1145 m, 1078 m, 1056 w, 943 m, 858 s, 745 s, 638 m, 601 m.

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