1-Butanol → 5-Methyl-2-(2',4'-dichloro-6'-methylanilino)phenylacetic acid

HRID 1242229Notes

Reaction equation

HRID 1242229 reaction equation
CN(C)[C:3](=[O:22])[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[NH:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=1[Cl:21].[OH-].[Na+].CCCC[OH:30].Cl>C1(C)C=CC=CC=1>[CH3:11][C:9]1[CH:8]=[CH:7][C:6]([NH:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=2[Cl:21])=[C:5]([CH2:4][C:3]([OH:22])=[O:30])[CH:10]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15541937N,N-dimethyl-5-methyl-2-(2',4'-dichloro-6'-methylanilino)phenylacetamide

Product 1

HCID 98620215-Methyl-2-(2',4'-dichloro-6'-methylanilino)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N,N-dimethyl-5-methyl-2-(2′,4′-dichloro-6′-methylanilino)phenylacetamide (1.5 g, 4.3 mmol) is hydrolyzed with 6N NaOH (70 ml) as a two phase solution with n-BuOH (40 ml) at reflux temperature for 14 hours. After cooling to room temperature, the mixture is poured over ice (100 ml). Toluene (100 ml) is added and the mixture transferred to a separatory funnel. The aqueous phase is brought to a pH of 1 with 3 N HCl. The organic phase is separated and the aqueous phase re-extracted with toluene (100 ml). The combined organic solution is dried (MgSO4) and concentrated under high vacuum (35–50 mbar), on a rotovap, taking care not to warm above 50°. Upon crystallization from Et2O/hexane, 5-methyl-2-(2′,4′-dichloro-6′-methylanilino)phenylacetic acid is obtained as a tan solid, m.p. 137–141°.

Workup

  1. temperatureat reflux temperature for 14 hours
  2. customthe mixture transferred to a separatory funnel
  3. customThe organic phase is separated
  4. extractionthe aqueous phase re-extracted with toluene (100 ml)
  5. dry with materialThe combined organic solution is dried (MgSO4)
  6. concentrationconcentrated under high vacuum (35–50 mbar), on a rotovap
  7. temperatureto warm above 50°
  8. customUpon crystallization from Et2O/hexane

Sources & evidence

ORD record
ord-2c5981d91e1c4583a307041aa31624b3
Source dataset
uspto-grants-2006_10
Patent number
US07115662B2

Reaction notes

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