Nitric Acid → HCID 14402878, compound

HRID 1381824Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].C(OC(=O)C)(=O)C.S(=O)(=O)(O)O.[C:17]([CH2:19][N:20]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[O:23][CH2:22][C:21]1=[O:30])#[N:18].[OH-].[Na+]>O>[C:17]([CH2:19][N:20]1[C:25]2[CH:26]=[C:27]([N+:1]([O-:4])=[O:2])[CH:28]=[CH:29][C:24]=2[O:23][CH2:22][C:21]1=[O:30])#[N:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Fuming (α 1.52) nitric acid (1.3 ml) is added dropwise to 0° C. to acetic anhydride (11.3 g), and thereafter a catalytic amount of concentrated sulfuric acid is added. To the solution is added portionwise at 0° C. 4-cyanomethyl-2H-1,4-benzoxazin-3(4H)-one (1.88 g). The mixture is stirred at 0° C. for 20 minutes, treated dropwise with a cold solution which is made by dissolving sodium hydroxide (10 g) in water (87.5 ml) and cooled to 0° C., stirred at 0° C. for 30 minutes to finish the reaction, and extracted with methyl isobutyl kotone. The extract is washed with water, dried, and evaporated. The resultant solid is recrystallized from ethanol to obtain an end product 4-cyanomethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (1.3 g). mp. 173° C.

Workup

additionTo the solution is added portionwise at 0° C
additiontreated dropwise with a cold solution which
temperaturecooled to 0° C.
stirringstirred at 0° C. for 30 minutes
customthe reaction
extractionextracted with methyl isobutyl kotone
washThe extract is washed with water
customdried
customevaporated
customThe resultant solid is recrystallized from ethanol

Sources & evidence

ORD record: ord-e15da29685884a71b7fef2dda3121417
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04804394

Reaction notes

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