O-Toluidine → HCID 178428815, compound

HRID 1583059Notes

Reaction equation

[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9](OC)(=[O:14])[CH2:10][C:11]([CH3:13])=O>>[CH3:13][C:11]1[CH:10]=[C:9]([OH:14])[C:5]2[C:3](=[C:2]([CH3:1])[CH:8]=[CH:7][CH:6]=2)[N:4]=1

Participants

Reactant 2

HCID 7242O-Toluidine

HCID 7757Methyl acetoacetate

Product 1

HCID 178428815HCID 178428815, compoundYield 38%

Procedure

Following a procedure similar to (454a), 2-methylaniline (21.4 g, 0.2 mol) was condensed with methyl acetoacetate (23.2 g, 0.2 mol) to provide the desired 2,8-dimethyl-4-hydroxyquinoline (456a) (13.0 g, 38%). MS (AP+): 173 (M+1).

Sources & evidence

ORD record: ord-d9fd9494313348f19c446c570f40ba5c
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740649B2

Reaction notes

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