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Triethylamine → Ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(2-nitrobenzenesulfonyloxy)-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 232488
Notes
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Reaction equation

HRID 232488 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16]([OH:19])[N:17]=2)[C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10]1.C(N(CC)CC)C.[N+:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43](Cl)(=[O:45])=[O:44])([O-:36])=[O:35].C(OCC)(=O)C>C(Cl)Cl.C(OCC)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16]([O:19][S:43]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[N+:34]([O-:36])=[O:35])(=[O:44])=[O:45])[N:17]=2)[C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 155402-Nitrobenzenesulfonyl chlorideHCID 178469556Ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 13922530Ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(2-nitrobenzenesulfonyloxy)-4-oxo-1,8-naphthyridine-3-carboxylate
Yield 97.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In 30 ml of methylene chloride was suspended 3.00 g of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-1,8-naphthyridine-3-carboxylate, and 1.02 g of triethylamine and 2.20 g of ortho-nitrobenzenesulfonyl chloride were added thereto with ice-cooling, after which the resulting mixture was subjected to reaction at the same temperature for 30 minutes and then at room temperature for 6 hours. The reaction mixture was washed with three 50-ml portions of water and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and to the residue thus obtained was added a mixture of 6 ml of ethyl acetate and 12 ml of diethyl ether, after which the crystals thus deposited were collected by filtration to obtain 4.40 g (yield 97.2%) of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(2-nitrobenzenesulfonyloxy)-4-oxo-1,8-naphthyridine-3-carboxylate having a melting point of 157°-160° C.

Workup

  1. additionwere added
  2. temperaturewith ice-cooling
  3. customafter which the resulting mixture was subjected to reaction at the same temperature for 30 minutes
  4. washThe reaction mixture was washed with three 50-ml portions of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customto the residue thus obtained
  8. additionwas added
  9. filtrationafter which the crystals thus deposited were collected by filtration

Sources & evidence

ORD record
ord-2ca9503282fc4cc9871466eca191a102
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04851535

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes