Hydrochloric Acid → Diisopropyl Ether

HRID 1415925

Reaction equation

HRID 1415925 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][N:9]2[C:12]2[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([F:21])=[CH:14][C:13]=2[F:22])=[CH:4][C:3]=1[F:29].Cl[CH2:31]Cl.[CH2:33]([OH:35])[CH3:34].Cl>[Pd].N1C=CC=CC=1>[CH:33]([O:35][CH:3]([CH3:4])[CH3:2])([CH3:31])[CH3:34].[NH2:18][C:16]1[CH:17]=[C:12]([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:29])=[C:2]([Cl:1])[N:11]=3)[C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8]2)[C:13]([F:22])=[CH:14][C:15]=1[F:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6344DichloromethaneHCID 15860361Ethyl 7-chloro-6-fluoro-1-(2,4-difluoro-5-nitrophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Product 2

HCID 7914Diisopropyl EtherHCID 53833255Ethyl 1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

Ethyl 7-chloro-6-fluoro-1-(2,4-difluoro-5-nitrophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (3.0 g) was added to a mixture of 50 ml of dichloromethane, 30 ml of ethanol, and 2 ml of conc. hydrochloric acid together with 280 mg of 10% palladium on carbon whereupon hydrogenation was carried out overnight at room temperature. Pyridine (2 ml) was added to the reaction solution, which was concentrated in vacua. To the residue were added 80 ml of chloroform and 10 ml of distilled water. The chloroform layer was separated, dried over anhydrous magnesium sulfate and then concentrated in vacua. Ethanol (8 ml) was added to the residue whereupon the solution was allowed to stand at room temperature. The precipitate was collected by filtration and washed with ethanol and then with diisopropyl ether to give 1.95 grams of the title compound.

Workup

  1. concentrationwas concentrated in vacua
  2. additionTo the residue were added 80 ml of chloroform and 10 ml of distilled water
  3. customThe chloroform layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacua
  6. additionEthanol (8 ml) was added to the residue whereupon the solution
  7. customto stand at room temperature
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-3d59db5f50eb48d6a61f086e4ee2c601
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Linked notes

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