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Formic Acid → 1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxylic acid

HRID 2111801
Notes
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Reaction equation

HRID 2111801 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:16][CH:15]=1)[C:7]([OH:9])=[O:8])([O-])=O.[CH:30](O)=O>C(OC)(OC)OC.C(Cl)Cl.[Fe]>[N:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[O:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:12]3[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=3[N:1]=[CH:30]2)=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 284Formic AcidHCID 690675383-Nitro-4-({4-[2-(pyridin-2-yloxy)ethoxy]phenyl}amino)benzoic acid

Product 1

HCID 576397141-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent
HCID 9005
Trimethyl orthoformate
Solvent

Procedure

3-Nitro-4-({4-[2-(pyridin-2-yloxy)ethoxy]phenyl}amino)benzoic acid (6.00 g, 15.20 mmol), iron powder (8.49 g, 152.00 mmol), and formic acid (68 mL) were dissolved in dry trimethyl orthoformate (175 mL). The reaction was allowed to stir at rt. After 18 h, the reaction mixture was diluted with CH2Cl2 and filtered through Celite to give a bright orange solid. The crude mixture was recrystallized from methanol to give 1-{4-[2-(pyridin-2-yloxy)ethoxy]phenyl}-1H-benzimidazole-5-carboxylic acid as a yellow-tan powder. 1H NMR (d6-DMSO, 400 MHz): δ 8.61 (d, J=2.4 Hz, 1H), 8.32 (d, J=1.6 Hz, 1H), 8.19 (ddd, J=5.2, 1.6, 0.8 Hz, 1H), 7.93 (dd, J=8.8, 1.6 Hz, 1H), 7.73 (ddd, J=8.8, 6.8, 1.8, Hz, 1H), 7.61 (ddd, J=4.8, 2.8, 2.8 Hz, 2H), 7.58 (s, 1H), 7.24 (ddd, J=5.2, 3.2, 3.2 Hz, 2H), 7.01 (ddd, J=6.8, 5.2, 1.2 Hz, 1H), 6.88 (dd, J=8.4, .4.0 Hz, 1H), 4.64 (t, J=4.2 Hz, 2H), 4.43 (t, J=4.6 Hz, 2H). MS(ES+): m/z 376.47 (10) [MH+].

Workup

  1. filtrationfiltered through Celite
  2. customto give a bright orange solid
  3. customThe crude mixture was recrystallized from methanol

Sources & evidence

ORD record
ord-ffa037b444fe4ec6a2847c2b58c768d6
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07521448B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes