Pyridine → 8-[3-[N-(acetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline

HRID 564953Notes

Reaction equation

HRID 564953 reaction equation
[Cl:1][C:2]1[C:20]([N:21]([C:23](=[O:26])[CH2:24][NH2:25])[CH3:22])=[CH:19][CH:18]=[C:17]([Cl:27])[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.[C:28](OC(=O)C)(=[O:30])[CH3:29].N1C=CC=CC=1>C(Cl)Cl>[C:28]([NH:25][CH2:24][C:23]([N:21]([C:20]1[C:2]([Cl:1])=[C:3]([C:17]([Cl:27])=[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)[CH3:22])=[O:26])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 117954848-[3-(N-glycyl-N-methylamino)2,6-dichlorobenzyloxy]-2-methylquinoline

Product 1

HCID 221131748-[3-[N-(acetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-[2,6-dichloro-3-(N-glycyl-N-methylamino)benzyloxy]-2-methylquinoline (100 mg), acetic anhydride (35 ml), pyridine (60 μl) and methylene chloride (2 ml) was stirred for 3 hours at ambient temperature. The reaction mixture was concentrated and the residue was purified by preparative thin-layer chromatography (ethyl acetate-methanol) to give 8-[3-[N-(acetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (138 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by preparative thin-layer chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-b7c1e4e53e254f25aad31abf7af35d5e
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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