Nitric Acid → 4,4-diethyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 899195Notes

Reaction equation

HRID 899195 reaction equation
[CH2:1]([C:3]1([CH2:14][CH3:15])[O:8][C:7](=[O:9])[NH:6][C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]1=2)[CH3:2].S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22]>C(O)(=O)C>[CH2:14]([C:3]1([CH2:1][CH3:2])[C:4]2[CH:13]=[C:12]([N+:21]([O-:23])=[O:22])[CH:11]=[CH:10][C:5]=2[NH:6][C:7](=[O:9])[O:8]1)[CH3:15]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 200422084,4-Diethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Product 1

HCID 200420994,4-diethyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred suspension of 4,4-diethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (6.00 g, 29.20 mmol) in a mixture of glacial acetic acid (25 mL) and concentrated sulfuric acid (25 mL) was slowly added concentrated nitric acid (5 mL). After stirring 10 minutes, the reaction mixture was quenched with a chilled brine solution (100 mL) and ice. A solid precipitated, which was collected on a filter and washed with water. After drying in vacuo, 4,4-diethyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one was obtained as a white solid (5.02 g, 69%). 1H NMR (DMSO-d6): δ 10.85 (s, 1H), 8.20 (dd, J=8.8, 2.5 Hz, 1H), 8.06 (d, J=2.4 Hz, 1H), 7.06 (d, J=8.8 Hz, 1H), 2.14 (m, 4H), 0.79 (t, J=7.3 Hz, 6H); MS (ESI) m/z 251 ([M+H]+); MS (ESI) m/z 249 ([M−H]−); Anal. calcd for C12H14N2O4: C, 57.59; H, 5.64; N, 11.19. Found: C, 57.44; H, 5.57; N, 11.16.

Workup

  1. customthe reaction mixture was quenched with a chilled brine solution (100 mL) and ice
  2. customA solid precipitated
  3. customwhich was collected on
  4. filtrationa filter
  5. washwashed with water
  6. customAfter drying in vacuo

Sources & evidence

ORD record
ord-05a14eac998543cf8db097095aed1e41
Source dataset
uspto-grants-2008_04
Patent number
US07354915B2

Reaction notes

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