Bromosuccinimide → HCID 13491950, compound

HRID 979784Notes

Reaction equation

HRID 979784 reaction equation
[CH3:1][N:2]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@@H:8]2[C@@H:3]1[CH2:4][C:5]1[C:6]3[C:19]([NH:20][CH:21]=1)=[CH:18][CH:17]=[CH:16][C:7]=32.[Br:22]C1CC(=O)NC1=O>C(Cl)(Cl)Cl>[Br:22][C:21]1[NH:20][C:19]2[C:6]3[C:5]=1[CH2:4][C@H:3]1[C@H:8]([C:7]=3[CH:16]=[CH:17][CH:18]=2)[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][N:2]1[CH3:1]

Participants

4

Reactant 2

HCID 38309BromosuccinimideHCID 10265374HCID 10265374, compound

Product 1

HCID 13491950HCID 13491950, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4 g of trans-4,6,6a,7,8,12b-hexahydro-7-methylindolo[4,3-ab]phenanthridine are suspended in 300 ml of chloroform, and the stirred suspension is heated to reflux temperature. A solution of 2.7 g of bromosuccinimide in 100 ml of chloroform is quickly added, and the clear reaction solution is then refluxed for a further hour. The cooled reaction solution is extracted with 1n aqueous sodium carbonate solution, the organic phases dried, concentrated and the evaporation residue chromatographed on silica gel with methylene chloride/methanol=95/5 (methylene chloride 10% saturated with NH3). The title compound is obtained. Its bis[base]fumarate is cryst allised from methanol (m.p. 235°-237°).

Workup

  1. temperaturethe stirred suspension is heated
  2. temperatureto reflux temperature
  3. temperaturethe clear reaction solution is then refluxed for a further hour
  4. customThe cooled reaction solution
  5. extractionis extracted with 1n aqueous sodium carbonate solution
  6. customthe organic phases dried
  7. concentrationconcentrated
  8. customthe evaporation residue chromatographed on silica gel with methylene chloride/methanol=95/5 (methylene chloride 10% saturated with NH3)

Sources & evidence

ORD record
ord-2f6cad15a8534e419bcdbef781b60b62
Source dataset
uspto-grants-1987_01
Patent number
US04634708

Reaction notes

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