Tetrahydrofuran → HCID 23337263, compound

HRID 2163328Notes

Reaction equation

HRID 2163328 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].C1COCC1.[C:21]1([Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>C(OCC)C>[OH:14][C:11]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 23337251HCID 23337251, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 23337263HCID 23337263, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension was prepared from 4.3 g. 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 phenylmagnesium 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; yielded = 2.4 g.

Workup

  1. customA suspension was prepared from 4.3 g
  2. temperaturewhile maintaining the temperature in the range 10°-15° C
  3. customThe resulting reaction mixture
  4. customthe ethereal layer decanted from the solids
  5. customThe ethereal layer was dried
  6. customthe ether removed
  7. customafter recrystallization from methanol
  8. customyielded = 2.4 g

Sources & evidence

ORD record
ord-b94cabd130e940ebb9ecc29d88e5234b
Source dataset
uspto-grants-1979_01
Patent number
US04133884

Reaction notes

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