Nitric Acid → 2-n-dodecyl-6-hydroxy-7-nitro-2H-1,4-benzoxazin-3-(4H)-one

HRID 280822Notes

Reaction equation

HRID 280822 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([CH:17]1[C:22](=[O:23])[NH:21][C:20]2[CH:24]=[C:25]([OH:28])[CH:26]=[CH:27][C:19]=2[O:18]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C(O)(=O)C>[CH2:5]([CH:17]1[C:22](=[O:23])[NH:21][C:20]2[CH:24]=[C:25]([OH:28])[C:26]([N+:1]([O-:4])=[O:2])=[CH:27][C:19]=2[O:18]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 212986812-n-dodecyl-6-hydroxy-2H-1,4-benzoxazin-3-(4H)-one

Product 1

HCID 212986862-n-dodecyl-6-hydroxy-7-nitro-2H-1,4-benzoxazin-3-(4H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Fumic nitric acid (δ1.52, 1.4 ml, 0.0336 mole) in acetic acid (16 ml) was added dropwise under stirring at 15° C. to 2-n-dodecyl-6-hydroxy-2H-1,4-benzoxazin-3-(4H)-one (11.2 g, 0.0336 mole) in acetic acid. The 2-n-dodecyl-6-hydroxy-2H-1,4-benzoxazin-3-(4H)-one (5.6 g, 44%) separated as orange prisms and was used as such.

Workup

  1. customThe 2-n-dodecyl-6-hydroxy-2H-1,4-benzoxazin-3-(4H)-one (5.6 g, 44%) separated as orange prisms

Sources & evidence

ORD record
ord-0638e33a9d064be78de86a1127b0d249
Source dataset
uspto-grants-1986_05
Patent number
US04591548

Reaction notes

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