Hydrochloric Acid → HCID 53863065, compound

HRID 268181Notes

Reaction equation

HRID 268181 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(=O)([O-])[O-:24].[Na+].[Na+]>O>[OH: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

6

Reactant 4

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

Product 1

HCID 53863065HCID 53863065, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.5 g. of sodium nitrite in 30 ml. of water is added over a 30 minute period at 90°-95°C. to a rapidly stirred 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 600 ml. of 0.05N hydrochloric acid. The solution is held at this temperature for 20 minutes longer, cooled, treated with an excess of sodium carbonate and the crude product is extracted into benzene. The benzene solution is concentrated to remove the solvent and the residue is purified by partition chromatography in order to obtain the pure 1,2,3,5,10,11a- hexahydro-7-hydroxy-10-methyl-11H-pyrrolo[2,1-c] [1,4]benzodiazepin- 11-one.

Workup

  1. temperaturelonger, cooled
  2. extractionthe crude product is extracted into benzene
  3. concentrationThe benzene solution is concentrated
  4. customto remove the solvent
  5. customthe residue is purified
  6. customby partition chromatography in order

Sources & evidence

ORD record
ord-0e05818cf58b4191926e702a57afa851
Source dataset
uspto-grants-1976_03
Patent number
US03947408

Reaction notes

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