Methylamine → HCID 10643064, compound

HRID 613639Notes

Reaction equation

HRID 613639 reaction equation
[Cl:1][C:2]1[C:20](/[CH:21]=[CH:22]/[CH2:23][N:24]2C(=O)C3=CC=CC=C3C2=O)=[CH:19][CH:18]=[C:17]([Cl:35])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.CN>C(Cl)(Cl)Cl.CO>[NH2:24][CH2:23]/[CH:22]=[CH:21]/[C:20]1[C:2]([Cl:1])=[C:3]([C:17]([Cl:35])=[CH:18][CH:19]=1)[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

5

Reactant 2

HCID 6329MethylamineHCID 10601564HCID 10601564, compound

Product 1

HCID 10643064HCID 10643064, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 8-[2,6-dichloro-3-((E)-3-phthalimido-1-propenyl)benzyloxy]-2-methylquinoline (43 mg) in chloroform (1 ml) was added 2M solution of methylamine in methanol (0.5 ml), and the mixture was stirred in the dark at ambient temperature overnight. The mixture was evaporated in vacuo, and the residue was purified by preparative thin layer chromatography to give 8-[3-((E)-3-amino-1-propenyl)-2,6-dichlorobenzyloxy]-2-methylquinoline (27 mg) as pale yellow amorphous.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-d4e63b6e5ec44184bc96baf553054a13
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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