2-Methylquinoline → HCID 57187471, compound

HRID 1088449Notes

Reaction equation

[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH3:3].[C:12]([NH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)(=[O:14])[CH3:13].[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH:3]=[CH:20][C:19]1[CH:22]=[CH:23][C:16]([N:15]([C:24](=[O:26])[CH3:25])[C:12](=[O:14])[CH3:13])=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 70602-Methylquinoline

HCID 7918Acetic Anhydride

HCID 739424-Acetamidobenzaldehyde

Product 1

HCID 57187471HCID 57187471, compound

Conditions

Temperature: 130 °C

Procedure

A mixture of quinaldine (10 ml) and 4-acetamidobenzaldehyde (12 g) in acetic anhydride (60 ml) was stirred at 130° C. for 2 days, then cooled to room temperature, evaporated to dryness and chromatographed on column of flash silica gel (800 g) using as solvent a mixture of hexane-ethyl acetate (1:1) to provide the title product as a yellow solid: m.p. 148-150° C.

Workup

temperaturecooled to room temperature
customevaporated to dryness
customchromatographed on column of flash silica gel (800 g)
additiona mixture of hexane-ethyl acetate (1:1)

Sources & evidence

ORD record: ord-993bd402651a4462a86899aeae978d65
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04962203

Reaction notes

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