Sodium Hydroxide → HCID 9796768, compound

HRID 382499Notes

Reaction equation

HRID 382499 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([F:11])[C:5]=1[N:12]1[C:20]2[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:22]>C(O)C>[CH3:21][C:17]1[CH:18]=[CH:19][C:20]([NH:12][C:5]2[C:4]([Cl:3])=[CH:9][C:8]([F:10])=[CH:7][C:6]=2[F:11])=[C:15]([CH2:14][C:13]([OH:22])=[O:1])[CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21938661HCID 21938661, compound

Product 1

HCID 9796768HCID 9796768, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a degassed solution of 1500 ml of absolute ethanol and 510 ml of 2N NaOH (1.02 mol) is added 150 g (0.51 mol) of N-(2′-chloro-4′,6′-difluorophenyl)-5-methyloxindole. The resultant mixture is degassed and heated to 60-65° for 2 hours. Most of the ethanol is removed under reduced pressure and then 4500 ml of water is added to the residue which is then washed three times with 1500 ml of toluene. The aqueous layer is cooled to 0° and adjusted to pH 6 using 1.2 N HCl. The solid is filtered off and washed with 100 ml of water and dried. Recrystallization from ethyl acetate and heptane gives 5-methy-2-(2′,4′-difluoro-6-chloroanilino)phenylacetic acid of Example 1(g).

Workup

  1. customThe resultant mixture is degassed
  2. temperatureheated to 60-65° for 2 hours
  3. customMost of the ethanol is removed under reduced pressure
  4. addition4500 ml of water is added to the residue which
  5. washis then washed three times with 1500 ml of toluene
  6. temperatureThe aqueous layer is cooled to 0°
  7. filtrationThe solid is filtered off
  8. washwashed with 100 ml of water
  9. customdried
  10. customRecrystallization from ethyl acetate and heptane

Sources & evidence

ORD record
ord-06e1c3b67eb34b499201ad38a25921ff
Source dataset
uspto-grants-2001_10
Patent number
US06310099B1

Reaction notes

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