Sodium hydride → HCID 59002969, compound

HRID 561128Notes

Reaction equation

HRID 561128 reaction equation
[H-].[Na+].[C:3]([NH:7][CH:8]=[C:9]([C:15](=[O:27])[C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([O:24][CH3:25])[C:17]=1F)[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:6])([CH3:5])[CH3:4]>CN(C=O)C>[C:3]([N:7]1[C:17]2[C:16](=[CH:21][C:20]([F:22])=[C:19]([F:23])[C:18]=2[O:24][CH3:25])[C:15](=[O:27])[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8]1)([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178472000ethyl 3-(tert-butylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)prop-2-enoate

Product 1

HCID 59002969HCID 59002969, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of NaH (5.61 g, 140 mmol, 60% in oil) in DMF (300 mL) was cooled to 0° C. and treated dropwise with ethyl 3-(tert-butylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate (42.02 g, 117 mmol) in DMF (100 mL). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was poured into ice water and the resulting precipitate was removed by filtration, washed with water and then dried to yield ethyl 1-tert-butyl-6,7-difluoro-1,4-dihydro-8-methoxy4-oxoquinoline-3-carboxylate (38.9 g, 98%) as a pale yellow solid.

Workup

  1. customthe resulting precipitate was removed by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-33af54e7a8f74b2493a59322d4a16c8f
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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