2-Chloroethylamine hydrochloride → HCID 178472006, compound

HRID 2396981Notes

Reaction equation

HRID 2396981 reaction equation
[CH3:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:3]=1[C:4]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].Cl.[Cl:25][CH2:26][CH2:27][NH2:28]>C(N(CC)CC)C>[CH3:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:3]=1[C:4]([C:6](=[CH:12][NH:28][CH2:27][CH2:26][Cl:25])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 97937372-Chloroethylamine hydrochlorideHCID 54293321Ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)3-ethoxyacrylate

Product 1

HCID 178472006HCID 178472006, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate (5.0 g), 2-chloroethylamine hydrochloride (1.74 g) and triethylamine (1.97 g), the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-(2-chloroethyl)aminoacrylate (5.52 g), which is then treated with 60% sodium hydride (0.72 g) as in Reference Example 22 to give ethyl 1-(2-chloroethyl)-5-methyl-6,7,8-trifluoro-l,4-dihydro-4-oxoquinoline-3-carboxylate (3.90 g), as colorless needles (recrystallized from ethyl acetate--n-hexane), m.p. 161.5°-163.5° C. (dec.)

Sources & evidence

ORD record
ord-9a5d3405a8ee445eb0ce150cf5977f28
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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