Ethanol → HCID 9861583, compound

HRID 603359Notes

Reaction equation

HRID 603359 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH3:20])=[CH:17][CH:18]=2)[CH2:13][C:12]1=[O:21].C([OH:24])C>O>[CH3:20][C:16]1[CH:17]=[CH:18][C:19]([NH:11][C:3]2[C:4]([F:10])=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=2[F:1])=[C:14]([CH2:13][C:12]([OH:21])=[O:24])[CH:15]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 57952167HCID 57952167, compound

Product 1

HCID 9861583HCID 9861583, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The suspension of 350 mg of N-(2′,3′,4′,6′-tetrafluorophenyl)-5-methyloxindole in 20 ml of ethanol and 5 ml of water is degassed by passing through nitrogen for 1.5 h. Then 260 mg of 30% aqueous sodium hydroxide is added and the mixture is heated to reflux for 6.5 hours. Most of the ethanol is then removed by distillation the mixture is cooled to room temperature followed by the slow addition of 1N hydrochloric acid (1.05 g) to reach a pH of about 3. The precipitate is then filtered, washed with ethanol/water (1:1) and dried in vacuo at room temperature affording the title product.

Workup

  1. customis degassed
  2. additionThen 260 mg of 30% aqueous sodium hydroxide is added
  3. temperaturethe mixture is heated
  4. temperatureto reflux for 6.5 hours
  5. customMost of the ethanol is then removed by distillation the mixture
  6. additionfollowed by the slow addition of 1N hydrochloric acid (1.05 g)
  7. filtrationThe precipitate is then filtered
  8. washwashed with ethanol/water (1:1)
  9. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-ffce5957ed064c9fa254cb475a622631
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Reaction notes

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