2-Nitropropane → HCID 14478920, compound

HRID 620005Notes

Reaction equation

HRID 620005 reaction equation
C[O-].[Na+].[N+](C(C)C)([O-])=[O:5].[CH3:10][C:11]1[C:18]([CH2:19]Br)=[CH:17][CH:16]=[C:15]([NH:21][C:22](=[O:24])[CH3:23])[C:12]=1[C:13]#[N:14]>CO>[C:22]([NH:21][C:15]1[CH:16]=[CH:17][C:18]([CH:19]=[O:5])=[C:11]([CH3:10])[C:12]=1[C:13]#[N:14])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 10942334Sodium MethoxideHCID 14478919HCID 14478919, compound

Product 1

HCID 14478920HCID 14478920, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide, 0.43 g, in 100 ml of methanol, was added 0.84 g of 2-nitropropane. After 15 min, 2 g of 2-methyl-3-bromomethyl-6-acetamidobenzonitrile was added and the resulting solution was stirred for 2.5 h at ambient temperature. The solvent was then evaporated at reduced pressure and the residue dissolved in chloroform. The chloroform solution was filtered, washed with H2O, dried and the solvent removed at reduced pressure. The residue was crystallized from chloroform-carbon tetrachloride to yield 0.8 g (53%) of product, m.p. 170°-173° C. NMR (CDCl3) 2.30 (3H, s, CH3CO--N), 2.90 (3H, s, CH3), 8.00 (1H, d, C--5H), 8.6 (1H, d, C--6H), 10.20 (1H, s, (CHO)d. Anal. calc'd for CH11H10N2O2.1/3H2O: C, 63.5; H, 4.84; N, 13.5. Found: C, 63.4; H, 5.00; N, 13.7.

Workup

  1. customThe solvent was then evaporated at reduced pressure
  2. dissolutionthe residue dissolved in chloroform
  3. filtrationThe chloroform solution was filtered
  4. washwashed with H2O
  5. customdried
  6. customthe solvent removed at reduced pressure
  7. customThe residue was crystallized from chloroform-carbon tetrachloride

Sources & evidence

ORD record
ord-7119c987ffdf4914bbf95d3170801949
Source dataset
uspto-grants-1989_04
Patent number
US04818753

Reaction notes

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