Formic Acid → HCID 59627529, compound

HRID 340618Notes

Reaction equation

HRID 340618 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C1COCC1.C(O)=O.[CH3:16][O:17][C:18]([C:20]1[CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH:23]=[C:24]([NH2:26])[CH:25]=1)=[O:19]>O>[CH3:16][O:17][C:18]([C:20]1[CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH:23]=[C:24]([NH:26][CH:1]=[O:3])[CH:25]=1)=[O:19]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 57850917Methyl 5-amino-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 59627529HCID 59627529, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Acetic anhydride (11.0 g, 108 mmol) was added to THF (15 mL) followed by addition of formic acid (5.09 g, 133 mmol). The mixture was heated to 65° C. for 2.5 hours, then cooled to room temperature. 5-Amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (5.0 g, 21 mmol) was added, and the reaction mixture was stirred for three hours at 70° C., then cooled to room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 5-formylamino-4′-methyl-biphenyl-3-carboxylic acid methyl ester, which was used directly in the next step without further purification.

Workup

  1. temperaturecooled to room temperature
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-86248ca9eddc4a50bbafeaba85e5399c
Source dataset
uspto-grants-2014_11
Patent number
US08895589B2

Reaction notes

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