Ammonium Hydroxide → HCID 53721589, compound

HRID 1733560Notes

Reaction equation

HRID 1733560 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:20]([CH3:21])[CH2:19][CH2:18][C@@:14]4([C:15]=2[C:16]=1[OH:17])[C@H:9]3[CH2:10][C@@H:11]([CH3:24])[C:12]([O:22]C)=[CH:13]4.[NH4+].[OH-]>Cl.CC(C)=O>[CH3:24][C@H:11]1[CH2:10][C@@H:9]2[C@:14]3([CH2:18][CH2:19][N:20]([CH3:21])[C@@H:8]2[CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:16]([OH:17])[C:15]3=2)[CH2:13][C:12]1=[O:22]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 86737418HCID 86737418, compound

Product 1

HCID 53721589HCID 53721589, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of (6) (2.54 g, 7.7 mmole) in 1 N HCl (30 ml) was heated on the steam bath for 30 minutes. The cooled solution was made basic with concentrated NH4OH and extracted with three portions of chloroform. The chloroform extracts were evaporated to give a crystalline residue. The residue was dissolved in hot acetone and cooled. Crystals (1.29 g) of the hemi-acetone solvate of (4a) were collected after cooling. Recrystallization from acetone gave analytically pure (4a) as hemi-acetone solvate, mp 166°-167°, identical with material prepared previously.

Workup

  1. extractionextracted with three portions of chloroform
  2. customThe chloroform extracts were evaporated
  3. customto give a crystalline residue
  4. temperaturecooled
  5. customCrystals (1.29 g) of the hemi-acetone solvate of (4a) were collected
  6. temperatureafter cooling
  7. customRecrystallization from acetone

Sources & evidence

ORD record
ord-878bd134763f42b49d14718f8fd57302
Source dataset
uspto-grants-1980_12
Patent number
US04242514

Reaction notes

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