3,5-Dimethylaniline → HCID 19735188, compound

HRID 326635Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[CH3:10][O:11][C:12]([C:14]#[C:15][C:16](OC)=[O:17])=[O:13]>>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:4]2[C:3]=1[C:16](=[O:17])[CH:15]=[C:14]([C:12]([O:11][CH3:10])=[O:13])[NH:5]2

Participants

Reactant 2

HCID 79493,5-Dimethylaniline

HCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 19735188HCID 19735188, compoundYield 3.3%

Procedure

Using the method described in Example 18a with 3,5-dimethylaniline (20 g) and dimethylacetylene dicarboxylate (23.4 g) as reagents gave methyl 5,7-dimethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (1.25 g), m.p. 227°-229° C. δ (360 MHz, DMSO-d6) 2.34 (3H, s, 7-Me), 2.74 (3H, s, 5-Me), 3.94 (3H, s, CH3O), 6.49 (1H, s, 3-H), 6.89 (1H, s, 6-H) and 7.54 (1H, s, 8-H).

Sources & evidence

ORD record: ord-51570dbe36af4e12b5dbfb198811dbad
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270309

Reaction notes

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