Ethanol → HCID 18473918, compound

HRID 564844Notes

Reaction equation

HRID 564844 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[O:4][C:5]([CH:19]([C:21]2[C:29]3[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH3:20])(C(OCC2C=CC=CC=2)=O)[C:6](=[O:8])[N:7]=1.C(O)C>[C].[Pd].O1CCCC1>[CH3:31][N:2]([CH3:1])[C:3]1[O:4][CH:5]([CH:19]([C:21]2[C:29]3[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH3:20])[C:6](=[O:8])[N:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 18473985HCID 18473985, compound

Product 1

HCID 18473918HCID 18473918, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl 2-dimethylamino-5-[1-(6-fluoroindol-3-yl)ethyl]-4-oxo-2-oxazolin-5-carboxylate (500 mg) was dissolved into 15 ml of a solution of ethanol and tetrahydrofuran in a ration of 5:1. 10% palladium-carbon (170 mg) was added. The whole was subjected to hydrogenation under normal temperature and normal pressure for 1.5 hours. The whole was stirred at 80° C. under nitrogen atmosphere for 1 hour and then filtered to remove the catalyst. The filtrate was concentrated to give 2-dimethylamino-5-[1-(6-fluoroindol-3-yl)ethyl]-2-oxazolin-4-one (340 mg).

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2ec48c0ee19c4fad97d46f8db58102b5
Source dataset
uspto-grants-2001_01
Patent number
US06169102A

Reaction notes

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