Hydrochloric Acid → HCID 54525598, compound

HRID 268182Notes

Reaction equation

HRID 268182 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.[ClH:22]>[O-]S([O-])(=O)=O.[Cu+2].O>[Cl:22][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 3

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

Product 1

HCID 54525598HCID 54525598, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×

Procedure

A solution of 3,9 g. of sodium nitrite in 30 ml. of water is added over 10 minutes with stirring to a cooled (-10°to 0°C.) mixture 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, 13 g. of CuSO4. 5H2O, 60 ml. of concentrated hydrochloric acid and 40 ml. of water. The mixture is stirred for one hour without cooling, poured into 80 ml. of concentrated ammonium hydroxide and extracted with benzene. The benzene layer is washed with water and concentrated to remove the solvent. The residue is purified by partition chromatography in order to obtain the pure 7-chloro-1,2,3,5,10,11a-hexahydro- 10-methyl-11H-pyrrolo[2,1-c] [1,4]benzodiazepin-11-one, which melts at 97°-99°C. The hydrochloride salt melts at 244°-246°C.

Workup

  1. temperaturea cooled
  2. addition(-10°to 0°C.) mixture of 11.5 g
  3. stirringThe mixture is stirred for one hour
  4. temperaturewithout cooling
  5. additionpoured into 80 ml
  6. extractionof concentrated ammonium hydroxide and extracted with benzene
  7. washThe benzene layer is washed with water
  8. concentrationconcentrated
  9. customto remove the solvent
  10. customThe residue is purified
  11. customby partition chromatography in order

Sources & evidence

ORD record
ord-6fa0bf4cfe3b482cb37e7b758eacc3ff
Source dataset
uspto-grants-1976_03
Patent number
US03947408

Reaction notes

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