Aniline → 2-Methoxy-1-naphthylidene-phenylamine

HRID 569246Notes

Reaction equation

HRID 569246 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1C=O.[C:15]1([NH2:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1>[CH3:1][O:2][CH:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[N:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 793522-Methoxy-1-naphthaldehyde

Product 1

HCID 201488432-Methoxy-1-naphthylidene-phenylamineYield 102.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Methoxy-1-naphthaldehyde [50.0 gm. 0.27 mole] and phenylamine [25 gm., 0.27 mole] were refluxed with benzene [100 ml] for 4 hours. The benzene was evaporated to an oil, dissolved in chloroform, the chloroform dried over sodium sulfate and evaporated to a green semi-solid of the 2-methoxy-1-naphthylidene-phenylamine [68.8 gm., 97% yield]

Workup

  1. customThe benzene was evaporated to an oil
  2. dissolutiondissolved in chloroform
  3. dry with materialthe chloroform dried over sodium sulfate

Sources & evidence

ORD record
ord-ab20b17bbc0f41cc88cebce9f28f81c7
Source dataset
uspto-grants-1988_03
Patent number
US04731457

Reaction notes

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