Sodium Hydroxide → 2-[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]ethanimidamide hydrochloride

HRID 867992Notes

Reaction equation

HRID 867992 reaction equation
[Cl:1][C:2]1[C:3]([O:21][CH2:22][C:23]#[N:24])=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3([CH2:18][CH2:19][CH3:20])[C:13]([C:14]=2[C:15]=1[Cl:16])=[CH:12][C:11](=[O:17])[CH2:10][CH2:9]3.C[O-].[Na+].[Cl-].[NH4+:29].[OH-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[C:3]([O:21][CH2:22][C:23](=[NH:29])[NH2:24])=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3([CH2:18][CH2:19][CH3:20])[C:13]([C:14]=2[C:15]=1[Cl:16])=[CH:12][C:11](=[O:17])[CH2:10][CH2:9]3

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 212895702-[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetonitrile

Product 1

HCID 212895732-[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]ethanimidamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetonitrile (200 mg, 0.549 mmole) in methanol (3 ml ) is added sodium methoxide (10 mg). After stirring for 1 hour ammonium chloride (53.5 mg, 1 mmole) is added and stirring is continued for 2 hours. The reaction mixture is poured into ice water containing 0.5 ml of 10N sodium hydroxide extracted with ether, washed with water dried over potassium carbonate, filtered and acidified with 10N ethanolic hydrochloric acid to precipitate 2-[(3,4-Dichloro-6,7,8,8a,8,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]ethanimidamide hydrochloride.

Workup

  1. additionis added
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. customto precipitate 2-[(3,4-Dichloro-6,7,8,8a,8,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]ethanimidamide hydrochloride

Sources & evidence

ORD record
ord-e37525cf3aea493084107c30d30c4048
Source dataset
uspto-grants-1988_10
Patent number
US04777281

Reaction notes

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