Water → HCID 53972344, compound

HRID 1418358Notes

Reaction equation

HRID 1418358 reaction equation
[OH-].[K+].[OH:3][NH:4]C(=O)OC(C)(C)C.[N+]([C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:16]=1[C:17]#[N:18])([O-])=O.O>CN(C=O)C>[NH2:18][C:17]1[C:16]2[C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=[CH:22][C:15]=2[O:3][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 97534tert-butyl N-hydroxycarbamateHCID 520718Dinitrobenzonitrile

Product 1

HCID 53972344HCID 53972344, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To potassium hydroxide (0.58 g, 10.3 mmol) and tert-butyl N-hydroxycarbamate (1.38 g, 10.3 mmol) in DMF (30 iml) was added 2,6-dinitrobenzonitrile (2.0 g, 10.3 nmmol) and the mixture was stirred for 20 h. Water was added. The whole was extracted with ether, the ether was dried (sodium sulphate) and evaporated. Flash column chromatography on silica gel, eluting with ethyl acetate/dichloromethane, gave the product (0.4 g), MS (+CI) 180 ([M+H]+), 1H NMR (CDCl3) 8.13 (1H, d), 7.78 (1H, d), 7.68 (1H, dd), 5.43 (2H, s).

Workup

  1. extractionThe whole was extracted with ether
  2. dry with materialthe ether was dried (sodium sulphate)
  3. customevaporated
  4. washFlash column chromatography on silica gel, eluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-2e3423ba87194d69a608968ddac9d485
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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