Aniline → HCID 86736420, compound

HRID 614636Notes

Reaction equation

HRID 614636 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:13](=[C:15]2\[C:16](=[C:22]([CH3:24])[CH3:23])[C:17](O[C:20]\2=[O:21])=[O:18])/[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH3:12][O:11][C:7]1[CH:6]=[C:5](/[C:13](=[C:15]2\[C:16](=[C:22]([CH3:23])[CH3:24])[C:17]([N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]\2=[O:21])=[O:18])/[CH3:14])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 6115AnilineHCID 86736421HCID 86736421, compound

Product 1

HCID 86736420HCID 86736420, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(E)-α-(3,4,5-trimethoxyphenyl) ethylideneisopropylidene succinic anhydride (4 parts), prepared as in Example 3, in toluene (40 parts by volume), and aniline (1 part) were heated (12 hours) at 70°. Petrol was added and the liberated succinamic acid separated. The dry acid (1.8 parts) was dissolved in acetyl chloride (40 parts by volume) boiled for 2 hours and the solvent removed. Crystallization of the product from a toluene/petrol mixture gave (E)-α-(3,4,5-trimethoxyphenyl) ethylideneisopropylidene-N-phenylsuccinimide as pale yellow needles, melting point 169.5°. The compound shows similar photochromic properties to the corresponding (E)-anhydride.

Workup

  1. customthe liberated succinamic acid separated
  2. dissolutionThe dry acid (1.8 parts) was dissolved in acetyl chloride (40 parts by volume)
  3. customthe solvent removed
  4. customCrystallization of the product from a toluene/petrol mixture

Sources & evidence

ORD record
ord-16adddc280874970aa250c30f64e4969
Source dataset
uspto-grants-1979_03
Patent number
US04145536

Reaction notes

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