Sodium Nitrite → 4-Hydroxy-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

HRID 29674노트

반응식

HRID 29674 반응식
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][C:5]=1[NH:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1.N([O-])=[O:27].[Na+]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([OH:27])=[CH:6][C:5]=1[NH:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 23668193Sodium NitriteHCID 692102524-Amino-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

생성물 1

HCID 692054424-Hydroxy-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester수율 83%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

This compound was produced using similar methods as those used in Step 3, example 27, starting with 4-amino-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (1.80 g, 5.08 mmol), trifluoroacetic acid (30 mL) and sodium nitrite (0.42 g, 6.15 mmol in 10 mL of water). The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 20/80) to give 4-hydroxy-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (1.49 g, 83%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6); δ 11.98 (s, 1H), 10.62 (s, 1H), 8.21 (d, 1H), 8.06 (d, 2H), 7.90 (d, 1H), 7.61 (d, 2H), 6.61 (dd, 1H), 3.84 (s, 3H).

후처리

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

출처 및 근거

ORD 기록
ord-cb13d3401329402c8f6b875e3a0243e4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420083B2

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