Benzenamine, 3-ethynyl- → HCID 787763, compound

HRID 1702157Notes

Reaction equation

HRID 1702157 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[C:15]([C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20])#[CH:16]>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:20]([C:19]3[CH:21]=[CH:22][CH:23]=[C:17]([C:15]#[CH:16])[CH:18]=3)[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 787763HCID 787763, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 10.7 g (0.10 mole) of 4-nitrophthalic anhydride in 150 ml of glacial acetic acid was added 12.9 g (0.11 mole) of 3-ethynylaniline. A white precipitate formed immediately. The mixture was heated to reflux for 1 hour, then cooled and filtered. The precipitate was washed with water and methanol. Recrystallization from toluene gave 25.7 g (87% yield) of 4-nitro-N-(3-ethynylphenyl)phthalimide, m.p. 257°-259° C.

Workup

  1. customA white precipitate formed immediately
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 1 hour
  4. temperaturecooled
  5. filtrationfiltered
  6. washThe precipitate was washed with water and methanol
  7. customRecrystallization from toluene

Sources & evidence

ORD record
ord-925afd8102ce44f697a3ed3a4ffaeed6
Source dataset
uspto-grants-1983_04
Patent number
US04380619

Reaction notes

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