Ammonia → HCID 20197300, compound

HRID 1414038Notes

Reaction equation

HRID 1414038 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[CH3:25][N:26]1CCCC1=O.N>C(OCC)(=O)C>[O:24]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22](=[O:23])[N:14]1[CH2:13][CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:25]#[N:26])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 20222394HCID 20222394, compound

Product 1

HCID 20197300HCID 20197300, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[3-[5-Bromo-1H-indol-3-yl]propyl]-1H-isoindole-1,3-(2H)-dione (8.43 g) and cuprous cyanide (3.2 g) were added to N-methyl-2-pyrrolidinone (20 ml) under a nitrogen atmosphere. The stirred mixture was heated to reflux over 25 min. and maintained at reflux for 45 min. It was then cooled to room temperature and poured onto ice-water (300 g). Concentrated aqueous ammonia (40 ml) and ethyl acetate (300 ml) were added and the mixture was stirred vigorously for 20 min. The brown organic layer was separated from the blue aqueous phase. The aqueous phase was then extracted with ethyl acetate (3×100 ml). The combined organic solutions were washed with water (3×100 ml) until the washings were colourless, dried (MgSO4) and evaporated in vacuo to afford a fawn solid (6.85 g), which was recrystallised from a mixture of isopropyl acetate (300 ml) and 2-propanol (100 ml) to afford the title compound as a pale fawn solid (5.2 g) m.p. 193°-195° C.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureto reflux over 25 min.
  3. temperaturemaintained
  4. temperatureat reflux for 45 min
  5. additionpoured onto ice-water (300 g)
  6. customThe brown organic layer was separated from the blue aqueous phase
  7. extractionThe aqueous phase was then extracted with ethyl acetate (3×100 ml)
  8. washThe combined organic solutions were washed with water (3×100 ml) until the washings
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-d549f48bec3446688eb6b495f6e1b725
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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