Tetrahydrofuran → 2'-Hydroxy-4'-methoxyacetanilide

HRID 132584

Reaction equation

HRID 132584 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[OH:12])([O-])=O.[H][H].[O:15]1CC[CH2:17][CH2:16]1>[Pd]>[OH:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[NH:1][C:16](=[O:15])[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2196355-Methoxy-2-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 41051392'-Hydroxy-4'-methoxyacetanilideYield 80%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
60 °C

Procedure

2-Nitro-5-methoxyphenol (R. J. Maleski, Synthetic Communications, 23(3), 343-348 (1993)) (48.5 g, 0.287 mol) dissolved in tetrahydrofuran (THF) (1.5 L) was hydrogenated at ambient temperature over night with 10% Pd/C (10 g) until 20.3 L of hydrogen was consumed. After filtration and evaporation the residue was suspended in degased water (1.7 L) and acetic anhydride (42.5 mL) was added with stirring. The mixture was heated to 60° C. for 1 h and then cooled. The isolated solid was washed thoroughly with water and dried in vacuo to give brick-red crystals (41.7 g, 80%).

Workup

  1. customwas consumed
  2. filtrationAfter filtration and evaporation the residue
  3. additionacetic anhydride (42.5 mL) was added
  4. temperaturecooled
  5. washThe isolated solid was washed thoroughly with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5b5ec7be27b84bcf93823c6d02e5c47e
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Linked notes

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