Formic Acid → HCID 69069868, compound

HRID 2111791Notes

Reaction equation

HRID 2111791 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[N+:21]([O-])=O)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[CH:24](O)=O>C(OC)(OC)OC.[Fe]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([N:11]2[C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=3[N:21]=[CH:24]2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 69064422HCID 69064422, compound

Product 1

HCID 69069868HCID 69069868, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 9005Trimethyl orthoformateSolvent

Procedure

A suspension of 4-{[3-(acetylamino)phenyl]amino}-3-nitrobenzoic acid (1.27 g, 4.04 mmol), Fe (1.77 g, 31.6 mmol, powder) in HCO2H (30 mL) and HC(OMe)3 (20 mL) was stirred under N2 at rt for 18 h. After this time, the reaction mixture was filtered through Celite, the cake washed with EtOH and the filtrate concentrated in vacuo. The resultant crude material was purified by column chromatography over silica gel eluting with 10% MeOH in DCM to afford 1-[3-(acetylamino)phenyl]-1H-benzimidazole-5-carboxylic acid. 1H NMR (400 MHz, DMSO-d6): δ 2.07 (s, 3H), 7.36 (d, J=8.4 Hz, 1H), 7.56 (t, J=8.0 Hz, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.96 (d, J=8.8 Hz, 1H), 8.02 (s, 1H), 8.34 (s, 1H), 8.71 (s, 1H), 10.3 (s, 1H); MS (ES+): m/z 296 [MH+]

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through Celite
  2. washthe cake washed with EtOH
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe resultant crude material was purified by column chromatography over silica gel eluting with 10% MeOH in DCM

Sources & evidence

ORD record
ord-495fe33b78e44fb494b8a8aa4007403c
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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