Pyridine → HCID 14054010, compound

HRID 846814Notes

Reaction equation

HRID 846814 reaction equation
N1C=CC=CC=1.[N+:7]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12])([O-:9])=[O:8].CN(C)C=O.C(Cl)(=O)C(Cl)=O.[C:28]([NH:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1)(=[O:32])[CH:29]([CH3:31])[CH3:30].[N+](C1C=CC=CC=1N)([O-])=O.N1C=CC=CC=1>C(OCC)(=O)C>[N+:7]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][C:38](=[O:39])[C:37]1[CH:36]=[CH:35][C:34]([NH:33][C:28](=[O:32])[CH:29]([CH3:30])[CH3:31])=[CH:42][CH:41]=1)([O-:9])=[O:8]

Participants

8

Reactant 6

HCID 1049PyridineHCID 6228DimethylformamideHCID 69462-NitroanilineHCID 65578Oxalyl chlorideHCID 5060504-(2-Methylpropanamido)benzoic acidHCID 86746071HCID 86746071, compound

Product 1

HCID 14054010HCID 14054010, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(2'-Nitrophenyl)-4-isobutyrylaminobenzamide is prepared under the reaction conditions given in Example 5: after the addition of pyridine/o-nitroaniline, the reaction solution is stirred for 15 hours at ambient temperature and for 5 hours at boiling temperature, the following components being used: 54.6 g (74.68 mMole) dimethylformamide, 1.5 L dry ethyl acetate, 37.3 g (29.42 mMole) oxalyl chloride, 47 g (22.63 mMole) 4-isobutyrylaminobenzoic acid, 34.4 g (24.89 mMole) o-nitroaniline, and 25.6 g (32.36 mMole) pyridine. The product is recrystallized from ethyl acetate. Yield 13.3 g (18% of theory); m.p. 237.6° C.

Workup

  1. customThe product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-075bae4af1d44d54a226c5ba3f700344
Source dataset
uspto-grants-1992_08
Patent number
US05137918

Reaction notes

Loading…