Hydrochloric Acid → HCID 21437928, compound

HRID 2397379Notes

Reaction equation

HRID 2397379 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:10][CH:9]=1.O.NN.[OH-].[K+].Cl>CCOCC.C1CCCCC1.O.C(O)COCCO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21437921HCID 21437921, compound

Product 1

HCID 21437928HCID 21437928, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8078CyclohexaneSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6.6 gm (0.018 mol) of ethyl 4-(2'-bromo-4-biphenylyl)-4-oxo-butyrate (m.p. 61°-62° C.), 3 gm of 100% hydrazine hydrate and 100 ml of diethyleneglycol was heated at 100° C. for 20 minutes. Then, 5 gm of pulverized potassium hydroxide were added. After refluxing for 5 hours, the reaction mixture was poured into 500 ml of water, acidified with dilute hydrochloric acid, and the precipitate was dissolved in ether. The ether solution was washed with water, dried and evaporated; the residue was dissolved in acetone, and by addition of cyclohexylamine the cyclohexylamine salt of 4-(2'-bromo-4-biphenylyl)-butyric acid, m.p. 148°-149° C. (from acetone), was obtained. Melting point of the free acid: 63° C. (from cyclohexane).

Workup

  1. temperatureAfter refluxing for 5 hours
  2. washThe ether solution was washed with water
  3. customdried
  4. customevaporated
  5. dissolutionthe residue was dissolved in acetone
  6. additionby addition of cyclohexylamine the cyclohexylamine salt of 4-(2'-bromo-4-biphenylyl)-butyric acid, m.p. 148°-149° C. (from acetone)
  7. customwas obtained

Sources & evidence

ORD record
ord-6e55bd921be04d2a809c8c8057e40391
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

Loading…