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

HRID 1042444Notes

Reaction equation

HRID 1042444 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-73d66d025b7d4bda9b0c4eccf9c31d86
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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