Acetic Acid → HCID 69213333, compound

HRID 899224Notes

Reaction equation

HRID 899224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:19])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:18])[O:9]2)=[CH:4][CH:3]=1.C(O)(=O)C.S(=O)(=O)(O)O.[N+:29]([O-])([OH:31])=[O:30]>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH3:19])[C:13]3[CH:14]=[C:15]([N+:29]([O-:31])=[O:30])[CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:18])[O:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 69213011HCID 69213011, compound

Product 1

HCID 69213333HCID 69213333, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred suspension of 4-(4-chlorophenyl)-4-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (5.15 g, 18.80 mmol) in a mixture of glacial acetic acid (15 mL) and concentrated sulfuric acid (15 mL) was slowly added concentrated nitric acid (3 mL). After 10 minutes the reaction was poured over ice and brine (100 mL) and filtered. Trituration of the solid with ethyl acetate/ether gave 4-(4-chlorophenyl)-4-methyl-6-nitro-1,4-dihydro-2H-3,1-benzoxazin-2-one as a tan solid (1.92 g, 32%). 1H NMR (DMSO-d6): δ 11.04 (s, 1H), 8.29 (m, 2H), 7.47 (dd, J=6.6, 2.0 Hz, 2H), 7.32 (dd, J=6.7, 2.1 Hz, 2H), 7.13 (d, J=9.5 Hz, 1H), 2.06 (s, 3H); MS (ESI) m/z [M+H]+(319/321); MS (ESI) m/z [M−H]−(317/319); Anal. calcd for C15H11ClN2O4: C, 56.53; H, 3.48; N, 8.79. Found: C, 55.43; H, 3.37; N, 8.78.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-c4a73457cdd64881ad12b7dc90d358d5
Source dataset
uspto-grants-2008_04
Patent number
US07354915B2

Reaction notes

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