Nitric Acid → N-(6-Nitro-1,3-benzodioxol-5-yl)acetamide

HRID 1669162Notes

Reaction equation

HRID 1669162 reaction equation
[N+:1]([O-:4])(O)=[O:2].[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[CH:13][C:8]=2[O:7][CH2:6]1>CC(O)=O>[N+:1]([C:11]1[C:12]([NH:14][C:15](=[O:17])[CH3:16])=[CH:13][C:8]2[O:7][CH2:6][O:5][C:9]=2[CH:10]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 98688N-(2H-1,3-Benzodioxol-5-yl)acetamide

Product 1

HCID 540215N-(6-Nitro-1,3-benzodioxol-5-yl)acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 70% HNO3 (15.5 mL, 244 mmol) in HOAc (40 mL) was added dropwise to a stirred solution of acetamide 218 (29.17 g, 163 mmol) in HOAc (150 mL) at 15-20° C. and the mixture stirred at 20° C. for 16 h. The precipitate was filtered, washed with water and dried to give nitroacetamide 219 (36.0 g, 99%) as a yellow powder: mp 207-208° C. (Krasso, A. & Ramuz, H., U.S. Pat. No. 4,599,347, 1986) mp 212-213° C.]; 1H NMR δ 10.78 (br s, 1H, NH), 8.36 (s, 1H, H-7), 7.66 (s, 1H, H-4), 6.10 (s, 2H, H-2), 2.27 (s, 3H, CH3).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-243ccca6062a483e889b8ae21989a5d6
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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