4-Aminophenol → HCID 59488862, compound

HRID 1960163Notes

Reaction equation

HRID 1960163 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][C:18]=1[N+:26]([O-:28])=[O:27]>CN(C=O)C>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[O:22])=[CH:19][C:18]=1[N+:26]([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 8471TriethylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 59488862HCID 59488862, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-phenol (12 g, 0.11 mol, Acros and Aldrich) was dissolved under an inert atmosphere, with stirring, in dry DMF (50 ml) and cooled in an ice-bath. Triethylamine (TEA, 11 g, 0.11 mol) was added and stirring continued for 1 hour. 4-Chloro-3-nitro-benzoyl chloride (22.2 g 0.1 mol, Acros and Aldrich) was added slowly and stirred overnight. The precipitated triethylamine.hydrochloride salt was filtered off and DMF removed under reduced pressure. The residue was extracted with EtOAc (3×100 ml) and citric acid (1M, 3×100 ml). The organic phase was dried with magnesium sulphate, filtered and evaporated to dryness under reduced pressure. The title product was recrystallised from methanol/water (1:1, 250 ml), yield 85%, and analysed by NMR and MS.

Workup

  1. temperaturecooled in an ice-bath
  2. stirringstirred overnight
  3. filtrationThe precipitated triethylamine.hydrochloride salt was filtered off
  4. customDMF removed under reduced pressure
  5. extractionThe residue was extracted with EtOAc (3×100 ml) and citric acid (1M, 3×100 ml)
  6. dry with materialThe organic phase was dried with magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure
  9. customThe title product was recrystallised from methanol/water (1:1, 250 ml), yield 85%

Sources & evidence

ORD record
ord-a1c76661032e47298dd134e6a5c6fbf5
Source dataset
uspto-grants-2013_04
Patent number
US08410312B2

Reaction notes

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