Acetic Acid → HCID 20545486, compound

HRID 2285597Notes

Reaction equation

HRID 2285597 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O.[C:20]([OH:23])(=O)[CH3:21].[N+:24]([O-])([OH:26])=[O:25]>C(OC(=O)C)(=O)C>[C:20]([NH:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]=1[N+:24]([O-:26])=[O:25])(=[O:23])[CH3:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 506896022483-35-8

Product 1

HCID 20545486HCID 20545486, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

1-Nitro-4-(2-phenoxy-ethoxy)-benzene is reduced and the resulting amine is heated in acetic anhydride and glacial acetic acid and nitrated with 70% strength nitric acid. 1-Acetamido-2-nitro-4-(2-phenoxy-ethoxy)-benzene is obtained in 90% yield (melting point: 104° to 106° C.). The amide is hydrolysed with potassium hydroxide in ethanol and the desired nitroamine is obtained in 98% yield (melting point 121° to 123° C.).

Sources & evidence

ORD record
ord-3c7c7874bbe04cebb84c7bbbc5c1cdc8
Source dataset
uspto-grants-1982_04
Patent number
US04323682

Reaction notes

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