1-Nitropropane → HCID 59145397, compound

HRID 2389262Notes

Reaction equation

HRID 2389262 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:17]=O)=[CH:4][CH:3]=1.P([O-])([O-])(O)=O.[NH4+].[NH4+].[N+:26](CCC)([O-])=O>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[C:17]#[N:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79031-NitropropaneHCID 24540Diammonium hydrogen phosphateHCID 4186278HCID 4186278, compound

Product 1

HCID 59145397HCID 59145397, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 33 (1.35 g 4.50 mmol), diammonium hydrogen phosphate (3.19 g, 23.8 mmol), 1-nitropropane (13.61 g, 152.9 mmol) and glacial acetic acid (10 mL) is refluxed overnight. During the reflux period, the pale-yellow mixture becomes dark red. The volatile reactants and solvents were removed under reduced pressure and an excess of water is then added to the dark residue. After a short time the crude 34 precipitated rapidly. It is separated by filtration washed with hexanes and dried under reduced pressure. Compound 34 was obtained as pale yellow solid in 1.19 g. MS (Es−ve) m/z 295.

Workup

  1. temperatureis refluxed overnight
  2. customThe volatile reactants and solvents were removed under reduced pressure
  3. additionan excess of water is then added to the dark residue
  4. customAfter a short time the crude 34 precipitated rapidly
  5. customIt is separated by filtration
  6. washwashed with hexanes
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-a66e5dcbd110456a9bafbf282135c01f
Source dataset
uspto-grants-2012_09
Patent number
US08273744B2

Reaction notes

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