Acetic Acid → o-(Methylamino)phenol

HRID 970317Notes

Reaction equation

HRID 970317 reaction equation
[BH4-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1.C(O)(=O)C>C1COCC1>[CH3:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9228BenzoxazoleHCID 4311764Sodium borohydride

Product 1

HCID 69138o-(Methylamino)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of sodium borohydride (4.77 g, 126.0 mmol) and benzoxazole (5.00 g, 42.0 mmol) in THF (150 mL) was added ˜1 mL of acetic acid. The reaction mixture was stirred overnight at room temperature and concentrated to dryness under reduced pressure. The excess sodium borohydride was decomposed with saturated aqueous ammonium chloride and extracted with EtOAc. The organic layer was collected, washed with water, washed with brine, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 104A in near quantitative yield. HPLC retention time=0.34 min. (Condition B). 1H-NMR (500 MHz, d6-DMSO) δ 2.69 (s, 3H), 4.70 (brs, 1H), 6.40-6.42 (m, 2H), 6.63-6.66 (m, 2H), and 9.12 (brs, 1H).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. extractionextracted with EtOAc
  3. customThe organic layer was collected
  4. washwashed with water
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-3af5efac85f84be3acfb0ccf0987e89a
Source dataset
uspto-grants-2007_12
Patent number
US07312209B2

Reaction notes

Loading…