Aniline → HCID 86736420, compound

HRID 2051703Notes

Reaction equation

HRID 2051703 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. Crystallisation 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. customCrystallisation of the product from a toluene/petrol mixture

Sources & evidence

ORD record
ord-9d7d5d26ea4b478ca65cab9addab03d4
Source dataset
uspto-grants-1980_01
Patent number
US04182629

Reaction notes

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