4-Aminophenol → 4-(4-Hydroxyanilino)-6-chloropyrimidine

HRID 1417990Notes

Reaction equation

HRID 1417990 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 8471TriethylamineHCID 709434,6-Dichloropyrimidine

Product 1

HCID 180091284-(4-Hydroxyanilino)-6-chloropyrimidineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,6-dichloropyrimidine (3.0 g), 4-aminophenol (2.2 g) and triethylamine (6 ml) in ethanol.(50 ml) was refluxed for 2 hours. The product so obtained was recrystallised from a mixture of ethyl acetate and hexane to give 6-chloro-4-(4'-hydroxyanilino)pyrimidine in 76% yield, m.p. 241-244° C.;

Workup

  1. temperature(50 ml) was refluxed for 2 hours
  2. customThe product so obtained
  3. customwas recrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-79faea1fd27c478ab1add66f871f0627
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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