Acetic Acid → 9-chloro-7-(2-chlorophenyl)-6,7-dihydro-2-methyl-5H-pyrimido[5,4-d][2] benzazepine dihydrochloride

HRID 464517Notes

Reaction equation

HRID 464517 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:21]=[C:20]([CH3:22])[N:19]=[CH:18][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.C(O)(=O)C>C(Cl)Cl.[Zn]>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:21]=[C:20]([CH3:22])[N:19]=[CH:18][C:7]=3[CH2:8][NH:9][CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 132255009-chloro-7-(2-chlorophenyl)-2-methyl-5H-pyrimido[5,4-d][2]benzazepine

Product 1

HCID 132255279-chloro-7-(2-chlorophenyl)-6,7-dihydro-2-methyl-5H-pyrimido[5,4-d][2] benzazepine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.7 g (10.5 mmole) of 9-chloro-7-(2-chlorophenyl)-2-methyl-5H-pyrimido[5,4-d][2]benzazepine, 1.3 g of zinc dust, and 40 ml of acetic acid in 90 ml of methylene chloride was stirred at -15° C. to -20° C. for 30 min. The mixture was filtered over hyflo, and the filtrate was basified with cold dilute aqueous sodium hydroxide and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. The yellow oil was crystallized from an excess of 6% methanolic hydrogen chloride to give the title compound as a white solid, mp 272°-274° C. Recrystallization from methanol gave colorless rods, mp 272°-274° C.

Workup

  1. filtrationThe mixture was filtered over hyflo
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customto give a yellow oil
  6. customThe yellow oil was crystallized from an excess of 6% methanolic hydrogen chloride

Sources & evidence

ORD record
ord-72957a9b05d04d178ae526177a071bc5
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

Loading…