Chloroacetyl chloride → 7-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 601505Notes

Reaction equation

HRID 601505 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C([O-])(O)=O.[Na+].Cl[CH2:18][C:19](Cl)=[O:20]>CC(C)CC(=O)C.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:19](=[O:20])[CH2:18][O:11][C:3]=2[CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
0 °C

Procedure

Mix 2-amino-5-nitro-phenol (10.0 g, 64.9 mmol) and NaHCO3 (13.1 g, 155.7 mmol) in 4-methyl-pentan-2-one (40 mL) and water (40 mL). Cool the mixture to 0° C. and slowly add chloroacetyl chloride (6.0 mL, 75.3 mmol) with stirring. After the addition is complete, reflux the mixture for 5 h. Cool the mixture to room temperature and let stand for 2.5 days. Collect the light yellow solid, wash with water and dry in a vacuum oven at 80° C. for 3 h. MS (ES−) 193.1 (M−1)−. 1H NMR (400 MHz, DMSO-d6): δ 11.31 (s, 1H), 7.90 (dd, 1H, J=8.8, 2.2 Hz), 7.76 (d, 1H, J=2.6 Hz), 7.06 (d, 1H, J=8.8 Hz), 4.72 (s, 2H).

Workup

  1. additionAfter the addition
  2. temperaturereflux the mixture for 5 h
  3. temperatureCool the mixture to room temperature
  4. customCollect the light yellow solid
  5. washwash with water
  6. customdry in a vacuum oven at 80° C. for 3 h

Sources & evidence

ORD record
ord-e3bfbb4d19a540e0b4d05fc0806afe6b
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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