N-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide → N-(2,3-dihydroxypropionyl)-3-amino-5-nitroaniline

HRID 261363Notes

Reaction equation

HRID 261363 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([CH:14]2[CH2:18][O:17]C(C)(C)[O:15]2)=[O:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1>C(O)(=O)C>[OH:15][CH:14]([CH2:18][OH:17])[C:12]([NH:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([NH2:1])[CH:3]=1)=[O:13]

Participants

3

Reactant 1

HCID 20394921N-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide

Product 1

HCID 20394926N-(2,3-dihydroxypropionyl)-3-amino-5-nitroaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.915 g (3.3 mmole) of N-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide in 20 ml of 50% acetic acid was heated on a steam bath for 1 hour then stored over a weekend. The solvents were removed in high vacuum to afford the product, N-(2,3-dihydroxypropionyl)-3-amino-5-nitroaniline, as an oil which was used without further purification.

Workup

  1. temperaturewas heated on a steam bath for 1 hour
  2. waitthen stored over a weekend
  3. customThe solvents were removed in high vacuum

Sources & evidence

ORD record
ord-adb1994d63cb49eeb2c26ef6f3c55bc1
Source dataset
uspto-grants-1979_08
Patent number
US04165365

Reaction notes

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