1-Boc-1-methylhydrazine → methyl 1-(N-tert-butoxycarbonyl-N-methylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1708544Notes

Reaction equation

HRID 1708544 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:9](=[O:20])[C:10]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[C:12]([F:18])[C:11]=1F)[C:5]([O:7][CH3:8])=[O:6].[C:22]([O:26][C:27]([N:29]([CH3:31])N)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[C:22]([O:26][C:27]([N:29]([N:2]1[C:11]2[C:10](=[CH:15][C:14]([F:16])=[C:13]([F:17])[C:12]=2[F:18])[C:9](=[O:20])[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3]1)[CH3:31])=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 37482801-Boc-1-methylhydrazineHCID 53884844Methyl 3-dimethylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylate

Product 1

HCID 18959448methyl 1-(N-tert-butoxycarbonyl-N-methylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To methylene chloride (120 ml) solution of methyl 3-dimethylamino -2-(2,3,4,5-tetrafluorobenzoyl)acrylate (13.2 g) was added methylene chloride (12 ml) solution of 1-tert-butoxycarbonyl-1-methylhydrazine (7.59 g) with ice-cooling, and the mixture was stirred for one hour at the same temperature and then for 15 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was triturated with diisopropyl ether (132 ml). The solid formed was taken out by filtration and dried with phosphorus pentaoxide under reduced pressure to obtain methyl 1-(N-tert-butoxycarbonyl-N-methylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (10.49 g).

Workup

  1. temperaturecooling
  2. waitfor 15 hours at room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was triturated with diisopropyl ether (132 ml)
  5. customThe solid formed
  6. filtrationwas taken out by filtration
  7. dry with materialdried with phosphorus pentaoxide under reduced pressure

Sources & evidence

ORD record
ord-cc0b7e2f8d064d019f7c36b789a8aaa5
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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