HCID 22759473, compound → HCID 22759442, compound

HRID 1704390Notes

Reaction equation

HRID 1704390 reaction equation
[BrH:1].[Cl:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[C:5]([Cl:12])[C:4]=1[CH:13]1[CH2:20][N:16]2[CH2:17][CH2:18][N:19]=[C:15]2[CH2:14]1.[H][H]>O.[Ni]>[BrH:1].[NH2:9][C:8]1[C:3]([Cl:2])=[C:4]([CH:13]2[CH2:20][N:16]3[CH2:17][CH2:18][N:19]=[C:15]3[CH2:14]2)[C:5]([Cl:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 22759473HCID 22759473, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22759442HCID 22759442, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A solution of 6-(2,6-dichloro-3-nitrophenyl)-2,3,6,7-tetrahydro-5H-pyrrolo[1,2-a]imidazole hydrobromide (2.3 g.) in water (70 ml.) is shaken with hydrogen in the presence of a Raney nickel catalyst (0.5 g.) at laboratory temperature and atmospheric pressure until uptake of hydrogen ceases. The mixture is filtered, the filtrate is evaporated to dryness and the residue is dissolved in hot ethanol (200 ml.). The solution is concentrated to 20 ml. by distillation and then cooled and filtered. There is thus obtained as solid residue 6-(3-amino-2,6-dichlorophenyl)-2,3,6,7-tetrahydro-5H-pyrrolo-[1,2-a]imidazole hydrobromide, m.p. 275°-277° C.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated to dryness
  3. dissolutionthe residue is dissolved in hot ethanol (200 ml.)
  4. concentrationThe solution is concentrated to 20 ml
  5. distillationby distillation
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-72d71c5f69b648b5852e035b1921c496
Source dataset
uspto-grants-1978_11
Patent number
US04126685

Reaction notes

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