Acetoacetic Acid → HCID 13550878, compound

HRID 745131Notes

Reaction equation

[N+:1]([C:4]([N+:21]([O-:23])=[O:22])([CH2:8][NH:9][CH2:10][C:11]([N+:18]([O-:20])=[O:19])([N+:15]([O-:17])=[O:16])[CH2:12][CH2:13][OH:14])[CH2:5][CH2:6][OH:7])([O-:3])=[O:2].CC([CH2:27][C:28]([OH:30])=[O:29])=O>>[C:6]([O:14][CH2:13][CH2:12][C:11]([N+:15]([O-:17])=[O:16])([N+:18]([O-:20])=[O:19])[CH2:10][N:9]([N+:1]([O-:3])=[O:2])[CH2:8][C:4]([N+:21]([O-:23])=[O:22])([N+:1]([O-:3])=[O:2])[CH2:5][CH2:6][O:7][C:28](=[O:30])[CH3:27])(=[O:7])[CH3:5].[C:28]([O:30][C:13](=[O:14])[CH3:12])(=[O:29])[CH3:27]

Participants

Reactant 2

HCID 96Acetoacetic Acid

HCID 23314310HCID 23314310, compound

Product 2

HCID 7918Acetic Anhydride

HCID 13550878HCID 13550878, compoundYield 90%

Procedure

The 3,3,7,7-tetranitro-5-azanonane-1,9-diol and its 1,9-diester derivatives are secondary amines with an active N-hydrogen which can be replaced with a more energetic group. For instance, Example 5 illustrate the nitration of the diacetate to form 3,3,5,7,7-pentanitro-5-azanonane-1,9-diol-1,9-diacetate using 90% nitric acid and acetic anhydride, ##STR19## Example 6 shows the acid hydrolysis of this diacetate to form 3,3,5,7,7-pentanitro-5-azanonane-1,9-diol, ##STR20##

Sources & evidence

ORD record: ord-644a8489c0674e7b8df5299b5998e470
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USH0000078

Reaction notes

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