Hydrochloric Acid → 2,3,4,5-Tetrahydro-1H-1-benzazepine-7,9-di-carboxylic acid

HRID 4933

Reaction equation

HRID 4933 reaction equation
C([O:8][C:9]([C:11]1[C:21]2[NH:20][CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[CH:14]=[C:13]([C:22]#N)[CH:12]=1)=[O:10])C1C=CC=CC=1.[OH-:24].[Na+].[OH2:26].C(O)C.Cl>O>[NH:20]1[C:21]2[C:11]([C:9]([OH:8])=[O:10])=[CH:12][C:13]([C:22]([OH:26])=[O:24])=[CH:14][C:15]=2[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19096565Water ethanolHCID 536812057-Cyano-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid benzyl ester

Product 1

HCID 197972052,3,4,5-Tetrahydro-1H-1-benzazepine-7,9-di-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-Cyano-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid benzyl ester (3.30 g) and sodium hydroxide (2 g) in a mixed solution of water-ethanol (1:1, 60 ml) was refluxed for 8 hours. After cooled, water (100 ml) was added to the reaction mixture, which was then rendered to have pH 3 with concentrated hydrochloric acid. The deposited crystal was collected by filtration, washed with water and dried to give the intended compound 1.84 g (85.0%), which was then recrystallized from ethanol to give slightly yellow crystal. M.P.: 287°-288° C.

Workup

  1. temperatureAfter cooled
  2. filtrationThe deposited crystal was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ca2fd54a918b4c22a80531e0a6588ec9
Source dataset
uspto-grants-1993_09
Patent number
US05242912

Linked notes

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