Acetyl chloride → HCID 18959442, compound

HRID 1708547Notes

Reaction equation

HRID 1708547 reaction equation
[OH:1][CH2:2][N:3]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:17])=[C:12]([F:16])[C:13]=2[F:15])[C:8](=[O:18])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6]1)[CH3:4].[CH2:24](N(CC)CC)[CH3:25].C(Cl)(=O)C>C(Cl)Cl.O>[CH2:24]([O:1][CH2:2][N:3]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:17])=[C:12]([F:16])[C:13]=2[F:15])[C:8](=[O:18])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6]1)[CH3:4])[CH3:25]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11067470ethyl 1-[N-(hydroxymethyl)-N-methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 18959442HCID 18959442, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 1-[N-(hydroxymethyl)-N-methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (8.4 g) and triethylamine (3.09 g) in methylene chloride (150 ml) was cooled to 0° C. and treated with acetyl chloride (2.18 g). After 3 hours the reaction was diluted with water and shaken in a separating funnel. The organic layer was dried over magnesium sulfate, evaporated, and the crude product purified by chromatography with silica gel (50% ethyl acetate-hexane elution) to yield ethyl 1-[N-(ethoxymethyl)-N-methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (2.1 g).

Workup

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. customevaporated
  3. customthe crude product purified by chromatography with silica gel (50% ethyl acetate-hexane elution)

Sources & evidence

ORD record
ord-82ce7ac0653145b3812866852b53b5c1
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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