n-Methyl-p-aminophenol → HCID 54163094, compound

HRID 616811Notes

Reaction equation

HRID 616811 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH:10](OCC)(OCC)OCC.[C:20](#[N:24])[CH2:21][C:22]#[N:23]>C(O)C.O>[C:22]([C:21](=[CH:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)[C:20]#[N:24])#[N:23]

Participants

6

Reactant 3

HCID 5931n-Methyl-p-aminophenolHCID 8010MalononitrileHCID 31214Ethyl orthoformate

Product 1

HCID 54163094HCID 54163094, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 62.5 grams (0.5 mole) of N-methyl-p-aminophenol, 74.0 grams (0.5 mole) of triethyl orthoformate, and 33.5 grams (0.5 mole) of malononitrile in 400 milliliters of 99.5% ethanol was prepared under a nitrogen atmosphere and heated at 75°-78° C. for 17 hours. The reaction mixture was cooled to room temperature, diluted with 1.5 liters of water plus ice and allowed to stand 1/2 hour. The precipitate was filtered to obtain 44 grams of α-cyano-β-(N-methyl-p-hydroxyanilino)acrylonitrile, melting point 187°-189° C. Five grams of this precipitate was treated with diethylsulfate in aqueous sodium hydroxide to obtain 0.5 gram of α-cyano-β-(N-methyl-p-ethoxyanilino)acrylonitrile (Formula II, supra) as a solid which melts at 147°-148° C. after recrystallization from ethyl acetate.

Workup

  1. customwas prepared under a nitrogen atmosphere
  2. temperatureheated at 75°-78° C. for 17 hours
  3. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-cafc00dc64d6484ca43a142411526a92
Source dataset
uspto-grants-1978_02
Patent number
US04076688

Reaction notes

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