Aniline → HCID 178438298, compound

HRID 979271Notes

Reaction equation

HRID 979271 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([C:11]12[CH2:17][CH:14]([CH:15]=[CH:16]1)[CH:13]1[C:18]([O:20][C:21](=[O:22])[CH:12]21)=[O:19])[CH:9]=[CH2:10]>>[C:2]1([N:1]=[C:21]([CH:12]2[CH:13]([C:18]([OH:20])=[O:19])[CH:14]3[CH2:17][C:11]2([CH2:8][CH:9]=[CH2:10])[CH:16]=[CH:15]3)[OH:22])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 54206110Allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride

Product 1

HCID 178438298HCID 178438298, compound

Conditions

Temperature
150 °C

Procedure

93 g of aniline are added dropwise to 102 g of allyl-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride, while stirring. During this addition, the temperature rises to 80° C. The mixture is heated to 150° C. and the pressure is reduced to 4,266 Pa. 9 ml of water and 46 ml of aniline distil off. Distillation gives 82.37 g (60% of theory) of a viscous yellow oil of boiling point 183° C. under 12 Pa, nD20 1.5738 and η25 105.6 Pa.s.

Workup

  1. additionDuring this addition
  2. customrises to 80° C
  3. custom9 ml of water and 46 ml of aniline distil off
  4. distillationDistillation
  5. customgives 82.37 g (60% of theory) of a viscous yellow oil of boiling point 183° C. under 12 Pa

Sources & evidence

ORD record
ord-49922f24ade541e2b8f5cd7927291618
Source dataset
uspto-grants-1987_05
Patent number
US04667003

Reaction notes

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