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

HRID 990923Notes

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]>>[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

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 516892Sodium Bicarbonate

HCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 91.3%

Procedure

This compound was prepared by General Method 1 from 2-amino-5-nitrophenol (6.0 g, 39 mmol), NaHCO3 (7.8 g, 93 mmol), and chloroacetyl chloride (3.58 mL, 45 mmol) to afford 6.91 g (91%) of 7-nitro-2H-1,4-benzoxazin-3(4H)-one. Data for 7-nitro-2H-1,4-benzoxazin-3(4H)-one: Rf 0.44 (11.5:1 CH2Cl2:MeOH); 1H NMR (400 MHz, DMSO-d6) δ 11.3 (br s, 1H), 7.90 (dd, 1H, J=8.7, 2.6), 7.76 (d, 1H, J=2.5), 7.06 (d, 1H, J=8.7), 4.73 (s, 2H).

Sources & evidence

ORD record: ord-77c36d31b08648b994ce5a907425cfc9
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462038B1

Reaction notes

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