Tetrahydrofuran → Ammonium Hydroxide

HRID 1925353Notes

Reaction equation

HRID 1925353 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=O)[CH2:8][O:7][C:6]=2[CH:12]=1.C1COCC1>O>[NH4+:10].[OH-:1].[O:7]1[CH2:8][CH2:9][NH:10][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:12][C:6]1=2

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 100578707-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 2

HCID 14923Ammonium HydroxideHCID 193865643,4-dihydro-2H-benzo[b][1,4]oxazin-7-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 7-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one (6 g, 36.36 mmol) in THF (50 mL) BH3-THF (150 mL, 254.54 mmol) was slowly added at RT. The resulting reaction was stirred for 4 h at 60° C. before water (5 mL) was added. The solution was concentrated in vacuo and purified with column chromatography using 100% CH2Cl2→25%→50% 90:10:1 CH2Cl2:MeOH:NH4OH to yield the title compound. MS (ESI, pos. ion) m/z: 152 (M+1). Mass calc'd for C8H9NO2: 151.06.

Workup

  1. customThe resulting reaction
  2. additionwas added
  3. concentrationThe solution was concentrated in vacuo
  4. custompurified with column chromatography

Sources & evidence

ORD record
ord-39f6e55abd9045c3a4aa96090188f9a9
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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