4-Chloroaniline → N-(p-chlorophenyl)valine

HRID 1389340Notes

Reaction equation

HRID 1389340 reaction equation
Br[CH:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[OH-].[Na+].CO.[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[OH-].[Na+]>C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1.CCOCC.CO>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C@H:2]([C:3]([OH:5])=[O:4])[CH:6]([CH3:8])[CH3:7])=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 78124-ChloroanilineHCID 112682-Bromoisovaleric acidHCID 14798Sodium HydroxideHCID 23721981Sodium hydroxide methanol

Product 1

HCID 13796078N-(p-chlorophenyl)valine

Reagents, catalysts & solvents 3

HCID 4764PhenolphthaleinCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of α-bromoisovaleric acid (2 g, 0.110 mole) and 5 ml of methanol is added one drop of phenolphthalein and then sufficient sodium hydroxide/methanol until adjusted to neutral pH. The solvent is then stripped off and p-chloroaniline (7 g, 0.055 mole) added. The mixture is melted in a 100° bath and stirred at 100° for 3 hours. The mixture is cooled and taken up in ether, and 10% aqueous sodium hydroxide is added. The aqueous phase is acidified to pH 4 and extracted with ether. The ether extracts are combined and washed with brine, dried over sodium sulfate and stripped to yield N-(p-chlorophenyl)valine.

Workup

  1. customis melted in a 100°
  2. temperatureThe mixture is cooled
  3. extractionextracted with ether
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-684edcf7fa5a419297b429eaf056657e
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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