Water → 2-(4-Nitro-phenyl)-1H-imidazo[4,5-b]pyridine-6-carboxylic acid

HRID 854097Notes

Reaction equation

HRID 854097 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:7]([NH2:22])=[N:6][CH:5]=1.O>C(O)CO.Cl.C(Cl)Cl.CO>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([C:11]2[NH:10][C:8]3[C:7]([N:22]=2)=[N:6][CH:5]=[C:4]([C:3]([OH:2])=[O:23])[CH:9]=3)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

6

Reactant 2

HCID 962WaterHCID 589329236-Amino-5-(4-nitro-benzoylamino)-nicotinic acid methyl ester

Product 1

HCID 589329162-(4-Nitro-phenyl)-1H-imidazo[4,5-b]pyridine-6-carboxylic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 174Ethylene GlycolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a suspension of 6-Amino-5-(4-nitro-benzoylamino)-nicotinic acid methyl ester (5) (4.05 g, 13 mmol) in ethylene glycol (300 ml) was added conc. HCl (20 drops) and the mixture heated at 160 C for 5 h. TLC in DCM/MeOH (19:1) indicates the absence of starting material. The solution was cooled and poured into H2O and the solid collected by filtration and air-dried. 1H NMR (500 MHz, DMSO-d6) δ14.08 (br s, 1H), 8.97 (s, 1H), 8.51 (br s, 1H), 8.49 (d, J=8.7 Hz, 2H), 8.43 (d, J=8.7 Hz, 2H), 3.92 (s, 3H). EIMS m/z M−1 297.3

Workup

  1. temperaturethe mixture heated at 160 C for 5 h
  2. temperatureThe solution was cooled
  3. filtrationthe solid collected by filtration
  4. customair-dried

Sources & evidence

ORD record
ord-74d2968f6af9406193dc9a5b96b0de7f
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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