Hydrochloric Acid → HCID 54523581, compound

HRID 268183Notes

Reaction equation

HRID 268183 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][C:9]2[N:15]([CH3:16])[C:14](=[O:17])[CH:13]3[CH2:18][CH2:19][CH2:20][N:12]3[CH2:11][C:10]=2[CH:21]=1.Cl.[C:23](=O)([O-])[O-:24].[Na+].[Na+]>O.CO>[CH3:23][O:24][C:6]1[CH:7]=[CH:8][C:9]2[N:15]([CH3:16])[C:14](=[O:17])[CH:13]3[CH2:18][CH2:19][CH2:20][N:12]3[CH2:11][C:10]=2[CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 53836685HCID 53836685, compound

Product 1

HCID 54523581HCID 54523581, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3.5 g. of sodium nitrite in 30 ml. of water is added over 1 hour at 48°-50°C. to a solution of 11.5 g. of 7-amino-1,2,3,5,10,11a-hexahydro-10-methyl-11H- pyrrolo[2,1-c] [1,4]benzodiazepin-11-one in 20 ml. of concentrated hydrochloric acid and 500 ml. of methanol. The reaction mixture is held at this temperature for 1 hour longer, diluted with an equal volume of water, neutralized with sodium carbonate and concentrated under reduced pressure to remove the methanol. The aqueous residue is extracted with benzene and the benzene layer is concentrated to remove the crude 1,2,3,5,10,11a-hexahydro-7-methoxy-10-methyl-11H- pyrrolo[2,1-c] [1,4]benzodiazepin-11-one. Further purification is by partition chromatography on a diatomaceous earth column using a heptane/methyl cellosolve solvent system.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the methanol
  3. extractionThe aqueous residue is extracted with benzene
  4. concentrationthe benzene layer is concentrated
  5. customto remove the crude 1,2,3,5,10,11a-hexahydro-7-methoxy-10-methyl-11H- pyrrolo[2,1-c] [1,4]benzodiazepin-11-one
  6. customFurther purification
  7. customby partition chromatography on a diatomaceous earth column

Sources & evidence

ORD record
ord-8040bac50f684f1ba384f7ede7c440c6
Source dataset
uspto-grants-1976_03
Patent number
US03947408

Reaction notes

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