Sodium Hydroxide → HCID 54187086, compound

HRID 2287468Notes

Reaction equation

[Cl:1][C:2]1[C:25]([N:26]([C:28](=[O:46])[CH2:29][NH:30][C:31](=[O:45])[CH:32]=[CH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([O:42]CC)=[O:41])=[CH:36][CH:35]=2)[CH3:27])=[CH:24][CH:23]=[C:22]([Cl:47])[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]=[C:11]2[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[OH-].[Na+]>C(O)C>[C:40]([C:37]1[CH:36]=[CH:35][C:34]([CH:33]=[CH:32][C:31]([NH:30][CH2:29][C:28]([N:26]([C:25]2[C:2]([Cl:1])=[C:3]([C:22]([Cl:47])=[CH:23][CH:24]=2)[CH2:4][O:5][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:15]=2[N:14]=[C:13]([CH3:16])[CH:12]=[C:11]3[N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH3:27])=[O:46])=[O:45])=[CH:39][CH:38]=1)([OH:42])=[O:41]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 8-[2,6-dichloro-3-[N-(4-ethoxycarbonylcinnamoylglycyl)-N-methylamino]benzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (64 mg), 1N sodium hydroxide solution (0.12 ml) in ethanol was stirred for 4 hours at 60° C. The mixture was concentrated in vacuo, and water was added to the residue. The solution was washed with diethyl ether, and the aqueous layer was adjusted to pH 5 with 1N hydrochloric acid. The resulting precipitate was collected by filtration and washed with water and diethyl ether to give 8-[3-[N-(4-carboxycinnamoylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (44 mg) as amorphous powder.

Workup

concentrationThe mixture was concentrated in vacuo, and water
additionwas added to the residue
washThe solution was washed with diethyl ether
filtrationThe resulting precipitate was collected by filtration
washwashed with water and diethyl ether

Sources & evidence

ORD record: ord-bbd7db81893e4ca684badfcdc0832bb1
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06083959

Reaction notes

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