Pyridine → HCID 10685269, compound

HRID 1839460Notes

Reaction equation

HRID 1839460 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([NH2:12])[C:8]([NH2:11])=[CH:9][CH:10]=1)=[O:4].N1C=CC=CC=1.[C:19]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25])#[N:20]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([NH:12][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([C:19]#[N:20])[CH:22]=2)[C:8]([NH2:11])=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 3084833-Cyanobenzoyl chloride

Product 1

HCID 10685269HCID 10685269, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-methoxycarbonyl-1,2-benzenediamine (8 g, 48 mmol) and pyridine (4 mL, 48 mmol) in acetonitrile (300 mL) at 0° C. was added 3-cyanobenzoyl chloride (8 g, 48 mmol). After 12 h, the reaction was concentrated and the residue was suspended with vigorous stirring in ethyl acetate (500 mL) and 1 M citric acid (200 mL). The solid was filtered, washed with diethyl ether and vacuum dried to give the title compound as an off-white solid (8 g, 56%); MS(FD): 295.1 (M+).

Workup

  1. concentrationthe reaction was concentrated
  2. filtrationThe solid was filtered
  3. washwashed with diethyl ether and vacuum
  4. customdried

Sources & evidence

ORD record
ord-5d273342efc8422a9775a2b77fab318f
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

Loading…