Bromide ion → HCID 23337263, compound

HRID 616586Notes

Reaction equation

HRID 616586 reaction equation
[NH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:11](=[O:14])[C:12](=[O:13])[N:4]([C:5]=23)[CH2:3][C:2]1=[O:15].[CH2:16]1[CH2:20]O[CH2:18][CH2:17]1.[Br-].[Cl-].[NH4+].[CH2:24](OCC)[CH3:25]>>[OH:14][C:11]1([C:16]2[CH:20]=[CH:25][CH:24]=[CH:18][CH:17]=2)[C:6]2[C:5]3[N:4]([CH2:3][C:2](=[O:15])[NH:1][C:10]=3[CH:9]=[CH:8][CH:7]=2)[C:12]1=[O:13]

Participants

6

Reactant 5

HCID 259Bromide ionHCID 3283Diethyl Ether2×HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 23337251HCID 23337251, compound

Product 1

HCID 23337263HCID 23337263, compound

Procedure

A suspension was prepared from 4.3 of 1H-pyrrolo[ 1,2,3-de]quinoxalin-2,5,6(3H)-trione in 200 ml. of THF. 16 ml. of a 2.83 M phentlmagnesium bromide solution in diethyl ether (phenyl Grignard reagent) were added thereto while maintaining the temperature in the range 10°-15° C. The resulting reaction mixture was stirred overnight after which time, 200 ml. of a saturated aqueous amonium chloride solution were added. An additional 1500 ml. of diethylether were added and the ethereal layer decanted from the solids. The ethereal layer was dried and the ether removed therefrom in vacuo. The resulting residue, comprising 6-hydroxy-6-phenyl-1H-pyrrolo[ 1,2,3-de]quinoxalin-2,5(3H,6H)-dione melted at 259°-62° C. with decomposition after recrystallization from methanol; yield = 2.4 g.

Workup

  1. temperaturewhile maintaining the temperature in the range 10°-15° C
  2. customThe resulting reaction mixture
  3. customthe ethereal layer decanted from the solids
  4. customThe ethereal layer was dried
  5. customthe ether removed
  6. customafter recrystallization from methanol

Sources & evidence

ORD record
ord-8f9edbf90237445e9977d339da72b99a
Source dataset
uspto-grants-1978_02
Patent number
US04075206

Reaction notes

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