Sodium Hydroxide → HCID 21082674, compound

HRID 347432Notes

Reaction equation

HRID 347432 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24]C)=[O:23])=[C:16]3[O:26][CH2:27][O:28][C:15]=13)=[CH:10][C:9]([O:29][CH3:30])=[C:8]([O:31][CH3:32])[CH:7]=2)#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])=[C:16]3[O:26][CH2:27][O:28][C:15]=13)=[CH:10][C:9]([O:29][CH3:30])=[C:8]([O:31][CH3:32])[CH:7]=2)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86604651HCID 86604651, compound

Product 1

HCID 21082674HCID 21082674, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl (2E)-3-[4(3-cyano-6,7-dimethoxyquinolin-4-ylamino)-2,3-methylenedioxyphenyl]acrylate (0.75 g), a 1N aqueous sodium hydroxide solution (12 ml) and methanol (45 ml) was stirred and warmed to 40° C. for 12 hours. The reaction mixture was evaporated. Water was added and the mixture was acidified by the addition of 2N aqueous hydrochloric acid solution. The resultant precipitate was isolated and dried. There was thus obtained the title compound as a solid (0.703 g); NMR Spectrum: (DMSOd6) 3.98 (s, 6H), 6.19 (s, 2H), 6.59 (d, 1H), 7.02 (d, 1H), 7.28 (d, 1H), 7.48 (s, 1H), 7.55 (d, 1H), 8.09 (s, 1H), 8.95 (s, 1H); Mass Spectrum: M+H+ 420.

Workup

  1. customThe reaction mixture was evaporated
  2. additionWater was added
  3. additionthe mixture was acidified by the addition of 2N aqueous hydrochloric acid solution

Sources & evidence

ORD record
ord-7dbe1a004e6346c9aacd870abd31d55e
Source dataset
uspto-grants-2007_02
Patent number
US07173135B2

Reaction notes

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