3-Aminophenol → HCID 54524025, compound

HRID 1417995Notes

Reaction equation

HRID 1417995 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1>C(Cl)Cl>[OH:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[NH:16][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 51046229HCID 51046229, compound

Product 1

HCID 54524025HCID 54524025, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-chloro-6-(3'-methylanilino)pyrimidine (9.56 g) and 3-aminophenol (5.22 g) was stirred and heated at 140° C. for 3 hours. The product so obtained was dissolved in methylene chloride and a few drops of methanol, and chromatographed on silica using a mixture of methylene chloride and methanol, increasing in polarity from pure methylene chloride to a 19:1 mixture of methylene chloride and methanol as eluent. The product so obtained was recrystallised from a mixture of ethyl acetate and hexane to give 4-(3'-hydroxyanilino)-6-(3'-methylanilino)pyrimidine in 39% yield, m.p. 188°-189° C.;

Workup

  1. customThe product so obtained
  2. customa few drops of methanol, and chromatographed on silica using
  3. additiona mixture of methylene chloride and methanol
  4. temperatureincreasing in polarity from pure methylene chloride to a 19:1 mixture of methylene chloride and methanol as eluent
  5. customThe product so obtained
  6. customwas recrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-71922d1d37464fe1a931186e3c008768
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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