Formic Acid → HCID 89995759, compound

HRID 523082Notes

Reaction equation

HRID 523082 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[O:20][CH3:21]>>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([NH:11][CH:1]=[O:3])=[C:13]([O:20][CH3:21])[CH:14]=1)#[N:17]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 118159314-Amino-3-methoxybenzonitrile

Product 1

HCID 89995759HCID 89995759, compound

Procedure

Acetic anhydride (0.65 mL, 6.7 mmol) was cooled in an ice bath and formic acid (0.38 mL, 10 mmol) was added with stirring. The ice-bath was removed and the mixture was stirred for a further 60 minutes. The reaction was re-cooled in the ice-bath and 4-amino-3-methoxybenzonitrile (0.25 g, 1.58 mmol) was added. The reaction was stirred at ice-bath temperature for 5 minutes, then at room temperature for 60 minutes. The reaction was concentrated in vacuo, azeotroped with toluene and the title compound was precipitated from ether/hexanes as a white powder (255 mg, 71.3%).

Workup

  1. customThe ice-bath was removed
  2. stirringthe mixture was stirred for a further 60 minutes
  3. additionwas added
  4. stirringThe reaction was stirred at ice-bath temperature for 5 minutes
  5. concentrationThe reaction was concentrated in vacuo
  6. customazeotroped with toluene
  7. customthe title compound was precipitated from ether/hexanes as a white powder (255 mg, 71.3%)

Sources & evidence

ORD record
ord-87df03ee17aa443bb2f859ee5e2c7350
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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