Sodium Hydroxide → HCID 135591770, compound

HRID 2118960Notes

Reaction equation

HRID 2118960 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:28])=[C:5]([C:23]2[O:24][CH:25]=[N:26][N:27]=2)[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[Cl:22])[C:7]=1[C:8]([O:10]CCC#N)=[O:9].[OH-].[Na+]>O.C(COC)OC>[CH3:1][C:2]1[NH:3][C:4]([CH3:28])=[C:5]([C:23]2[O:24][CH:25]=[N:26][N:27]=2)[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[Cl:22])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 135591771HCID 135591771, compound

Product 1

HCID 135591770HCID 135591770, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

30 g of the 2-cyanoethyl 1,4-dihydro-2,6-dimethyl-4-(2,3-dichlorophenyl)-5-(1,3,4-oxadiazol-2-yl)-pyridine-3-carboxylate thus prepared are stirred in a solution of 8.7 g of NaOH in 220 ml of water and 110 ml of dimethoxyethane for 3 hours at room temperature. The mixture is diluted with 200 ml of water and is extracted by shaking with three times 100 ml of CH2Cl2. The water phase is acidified by adding concentrated hydrochloric acid. The precipitate which has been deposited is then filtered off with suction, washed with water until it is neutral and dried in vacuo at 50° C. This gives 22.0 g (corresponding to 91.1% of theory) of 1,4-dihydro-2,6-dimethyl-4-(2,3-dichlorophenyl)-5-(1,3,4-oxadiazol-2-yl)-pyridine-3-carboxylic acid of melting point 187°-190° C. Analysis:

Workup

  1. extractionis extracted
  2. additionby adding concentrated hydrochloric acid
  3. filtrationThe precipitate which has been deposited is then filtered off with suction
  4. washwashed with water until it
  5. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-c26113e0ad93463b84d41ac119283c10
Source dataset
uspto-grants-1987_07
Patent number
US04681891

Reaction notes

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