Potassium Hydroxide → HCID 20298406, compound

HRID 1389228Notes

Reaction equation

HRID 1389228 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13].[OH-].[K+]>C1C=CC=CC=1.C(O)C>[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20298423HCID 20298423, compound

Product 1

HCID 20298406HCID 20298406, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A solution of 8.0 g of ethyl 5-(biphenyl-2-yl)amino-valerate (see Example 53) in 60 ml of benzene is mixed with a solution of 2.2 g of potassium hydroxide in 20 ml of ethanol. After allowing the resulting admixture to stand for 24 hours at room temperature, the solvent mixture is distilled off in vacuo. The residue is then dissolved in water; the obtained aqueous solution is washed with diethyl ether and then acidified with dilute hydrochloric acid. The formed precipitate, which is oily at first, is taken up in dichloromethane. The solvent is then distilled off and the residue recrystallized from ethyl acetate/petrol ether (1:1) to obtain 5.6 g (77.3% of theory) of 5-[N-(biphenyl-2-yl)amino]valeric acid, MP 73° to 75°.

Workup

  1. distillationthe solvent mixture is distilled off in vacuo
  2. dissolutionThe residue is then dissolved in water
  3. washthe obtained aqueous solution is washed with diethyl ether
  4. distillationThe solvent is then distilled off
  5. customthe residue recrystallized from ethyl acetate/petrol ether (1:1)

Sources & evidence

ORD record
ord-860fde0f2e4647258f1cb38c2b035988
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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