Formic Acid → HCID 69069868, compound

HRID 2111809Notes

Reaction equation

HRID 2111809 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) and iron powder (1.77 g, 31.6 mmol) in HCO2H (30 mL) and HC(OMe)3 (20 mL) was stirred at rt under N2 atmosphere. After 18 h, the reaction mixture was filtered through Celite and the Celite pad was washed with EtOH. The solvent was removed in vacuo. The resultant crude material was purified by silica gel chromatography (10% MeOH in CH2Cl2) to afford 1-[3-(acetylamino)phenyl]-1H-benzimidazole-5-carboxylic acid as a light yellow solid. 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. filtrationthe reaction mixture was filtered through Celite
  2. washthe Celite pad was washed with EtOH
  3. customThe solvent was removed in vacuo
  4. customThe resultant crude material was purified by silica gel chromatography (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5080df58307e4ea896ac98da9ca9a6e9
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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