1-Chloroethyl chloroformate → 6,7,8,9-tetrahydro-1H-pyrrolo[2,3-f]isoquinoline-2,3-dione

HRID 1648239Notes

Reaction equation

HRID 1648239 reaction equation
C[N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[C:14](=[O:15])[C:13](=[O:16])[NH:12][C:8]3=2)[CH2:3]1.ClC(OC(Cl)=O)C>ClCCCl>[NH:12]1[C:8]2=[C:9]3[C:4](=[CH:5][CH:6]=[C:7]2[C:14](=[O:15])[C:13]1=[O:16])[CH2:3][NH:2][CH2:11][CH2:10]3

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 152882036,7,8,9-tetrahydro-7-methyl-1H-pyrrolo[2,3-f]isoquinoline-2,3-dione

Product 1

HCID 152882046,7,8,9-tetrahydro-1H-pyrrolo[2,3-f]isoquinoline-2,3-dione

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To an ice cooled stirred suspension of 6,7,8,9-tetrahydro-7-methyl-1H-pyrrolo[2,3-f]isoquinoline-2,3-dione (500 mg) in 1,2-dichloroethane (10 ml) was added α-chloroethylchloroformate (0.25 ml). The mixture was then brought to reflux for 1 hour, whereafter it was cooled to room temperature and filtered. The filtrate was evaporated, the residue dissolved in methanol (10 ml) and refluxed for 10 min. Evaporation of the solvent left the crude title compound as a solid, M.p. 270° C.

Workup

  1. temperatureto reflux for 1 hour, whereafter it
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. dissolutionthe residue dissolved in methanol (10 ml)
  5. temperaturerefluxed for 10 min
  6. customEvaporation of the solvent
  7. waitleft the crude title compound as a solid, M.p. 270° C.

Sources & evidence

ORD record
ord-19dd2e371e464c27bc6e1f55fee1a850
Source dataset
uspto-grants-1995_07
Patent number
US05436250

Reaction notes

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