Potassium Carbonate → 4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-7-ethynylquinoline

HRID 52447Notes

Reaction equation

HRID 52447 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[NH:5][C:4](=[O:18])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].CC1(C)C2C(=CC=C(C#C)C=2)NC(=O)C1>CO>[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[NH:5][C:4](=[O:18])[CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19963713HCID 19963713, compound2×HCID 199637324,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-7-[(trimethylsilyl)ethynyl]quinoline2×

Product 1

HCID 199637164,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-7-ethynylquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.77 g (6.5 mmol) of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-7-[(trimethylsilyl)ethynyl]quinoline (Compound 19), and 175 mg (1.3 mmol) of K2CO3 in 60 ml of methanol were reacted substantially in accordance with the procedure used for the preparation of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-ethynylquinoline (Compound 3), to give the title compound as an orange oil. The product was used in the next reaction without further purification.

Sources & evidence

ORD record
ord-5eb9db8073734a27af4e570811d5fb39
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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