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

HRID 1042444노트

반응식

HRID 1042444 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 668556182-Propylamino-4-(trifluoromethyl)benzoic acid수율 18%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-73d66d025b7d4bda9b0c4eccf9c31d86
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557872B2

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