Acetic Acid → 2-Propylamino-4-(trifluoromethyl)benzoic acid

HRID 1042444ノート

反応式

HRID 1042444 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](O)(=O)[CH3:16].[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:19]([NH:1][C:2]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH2:15][CH3:16]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 678694-(Trifluoromethyl)anthranilic acidHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 668556182-Propylamino-4-(trifluoromethyl)benzoic acid収率 18%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Amino-4-(trifluoromethyl)benzoic acid (714 mg, 3.48 mmol), propionylaldehyde (0.27 ml, 3.74 mmol), acetic acid (3.49 mmol) and sodium triacetoxyborohydride (1.12 g, 5.25 mmol) were added in THF (40 ml). The reaction mixture was stirred overnight. The reaction mixture was quenched by adding sat. NaHCO3 (50 ml). The aqueous mixture was extracted with CH2Cl2 (30 ml×3). A combined organic layer was dried over MgSO4, concentrated in vacuo, and purified with column chromatography to yield title compound (155 mg, 18%).

後処理

  1. customThe reaction mixture was quenched
  2. additionby adding sat. NaHCO3 (50 ml)
  3. extractionThe aqueous mixture was extracted with CH2Cl2 (30 ml×3)
  4. dry with materialA combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified with column chromatography

出典と根拠

ORDレコード
ord-73d66d025b7d4bda9b0c4eccf9c31d86
出典データセット
uspto-grants-2013_10
特許番号
US08557872B2

反応ノート

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