Cyclopropylamine → HCID 12953788, compound

HRID 1703186Notes

Reaction equation

HRID 1703186 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]3[C:17]([O:19][C:20](=O)[C:8]=23)=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:22]1([NH2:25])[CH2:24][CH2:23]1>>[CH:22]1([N:25]2[C:17](=[O:18])[C:9]3[CH:10]=[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]4=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:8]=3[C:20]2=[O:19])[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 2266661-Phenyl-2,3-naphthalenedicarboxylic anhydride

Product 1

HCID 12953788HCID 12953788, compound

Procedure

1-Phenyl-2,3-naphthalenedicarboxylic anhydride (3.0 g) and cyclopropylamine (5 ml) were shaken for 5 minutes. The reaction mixture became very warm and excess cyclopropylamine was evaporated in vacuo. The solid remaining was then heated at 220° to 240° for 5 minutes in a nitrogen atmosphere. The solid formed was allowed to cool and was recrystallised from light petroleum (b.p. 40°-60°)/chloroform to give 2-cyclopropyl-1,3-dioxo-4-phenylbenz[f]isoindoline, (2.7 g, m.p. 198°).

Workup

  1. temperatureThe reaction mixture became very warm
  2. customexcess cyclopropylamine was evaporated in vacuo
  3. temperatureThe solid remaining was then heated at 220° to 240° for 5 minutes in a nitrogen atmosphere
  4. customThe solid formed
  5. temperatureto cool
  6. customwas recrystallised from light petroleum (b.p. 40°-60°)/chloroform

Sources & evidence

ORD record
ord-4e43e1781c984964b9b4263ee5f94e77
Source dataset
uspto-grants-1982_09
Patent number
US04351842

Reaction notes

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