Diazomethane → 4-[3-(7-Fluoro-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid methyl ester

HRID 1721172Notes

Reaction equation

HRID 1721172 reaction equation
[N+](=[CH2:3])=[N-].[F:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([CH2:15][O:16][C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:34])[CH2:25][C:26]([CH2:32][CH3:33])([CH2:30][CH3:31])[C:27]([OH:29])=[O:28])[CH:20]=[CH:21][CH:22]=3)=[N:12]2)=[CH:7][CH:6]=1>C(OCC)C.O1CCCC1>[CH3:3][O:28][C:27](=[O:29])[C:26]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:25][C:24]([NH:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH2:15][C:11]2[CH:10]=[CH:9][C:8]3[C:13](=[CH:14][C:5]([F:4])=[CH:6][CH:7]=3)[N:12]=2)[CH:18]=1)=[O:34]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 9888588Cgp 57698

Product 1

HCID 538783774-[3-(7-Fluoro-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of diazomethane in diethyl ether is added at 0° to a solution of 1.9 g of 4-[3-(7-fluoro-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid (Example 3) in 150 ml of tetrahydrofuran until a yellow colour remains established. The yellow solution is immediately concentrated by evaporation to give the title compound in the form of a colourless oil which crystallises on being left to stand in a refrigerator, m.p. 92°-93°; IR (methylene chloride): 1735 cm-1 (C=O).

Workup

  1. concentrationThe yellow solution is immediately concentrated by evaporation

Sources & evidence

ORD record
ord-a8f63b76dffa4de0ac765235a9c6820e
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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