2-Amino-3-Nitrophenol → HCID 16412775, compound

HRID 1441822Notes

Reaction equation

HRID 1441822 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12](C(CC)(CC)C([O-])([O-])[O-])[CH3:13]>>[CH3:12][C:13]1[O:11][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=2[N:1]=1

Participants

3

Reactant 2

HCID 41154952-Amino-3-NitrophenolHCID 21875354Triethylorthoaceate

Product 1

HCID 16412775HCID 16412775, compoundYield 95.1%

Conditions

Temperature
100 °C

Procedure

To 2-amino-3-nitrophenol (6.17 g, 40.0 mmol) was added triethylorthoacetate (25.96 g, 160.0 mmol) and the mixture was heated at 100° C. for 12 h to give a dark red solution. Cooling to room temperature produced a crystalline mass which was filtered and washed with hexane to give compound 474A (6.78 g, 95%) as light maroon needles. HPLC: 98.1% at 1.86 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 179.08 [M+H]+.

Workup

  1. customto give a dark red solution
  2. temperatureCooling to room temperature
  3. customproduced a crystalline mass which
  4. filtrationwas filtered
  5. washwashed with hexane

Sources & evidence

ORD record
ord-38ea64305a5348fba32101b46b1dbd44
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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