Thionyl Chloride → HCID 178461307, compound

HRID 1826911Notes

Reaction equation

HRID 1826911 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12]C(C2C=NC3C(C=2Cl)=CC(F)=CC=3F)=O)[CH2:8][CH2:7]1>C(N(CC)CC)C>[ClH:3].[CH3:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178461359HCID 178461359, compound

Product 1

HCID 178461307HCID 178461307, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Hydrolysis of ethyl 4-chloro-6,8-difluoroquinoline-3-carboxylate afforded 10.5 g of crude 4-hydroxy-6,8-difluoroquinoline-3-carboxylic acid hydrochloride. The crude acid (2 g,), thionyl chloride, trans-4-methylcyclohexylamine hydrochloride (748 mg, 5 mmol), and triethylamine (0.3 mLs) afforded crude N-(trans-4-methylcyclohexyl)-4-chloro-6,8-difluoroquinoline-3-carboxamide.

Sources & evidence

ORD record
ord-af69076275114a46999eb20483c5d806
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

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