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

HRID 29674ノート

反応式

HRID 29674 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-cb13d3401329402c8f6b875e3a0243e4
出典データセット
uspto-grants-2008_09
特許番号
US07420083B2

反応ノート

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