Pivaloyl chloride → HCID 69708999, compound

HRID 896354Notes

Reaction equation

HRID 896354 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[N+:15]([O-:17])=[O:16].[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>N1C=CC=CC=1>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[C:8]([N+:15]([O-:17])=[O:16])[CH:9]=1)#[N:12]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 22349296HCID 22349296, compound

Product 1

HCID 69708999HCID 69708999, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-(4-hydroxy-butylamino)-3-nitro-benzonitrile (10.0 g, 42.5 mmol) in pyridine (100 mL) was cooled to 0° C. under nitrogen. Pivaloyl chloride (5.8 mL, 47 mmol) was dropwise added and the resulting solution allowed to warm to room temperature and stirred overnight. The solvent was removed in vacuo and the residue stripped with toluene. The residue was suspended in ethyl acetate, filtered, and the filtrated concentrated to give 2,2-dimethyl-propionic acid 4-(4-cyano-2-nitro-phenylamino)-butyl ester (13.3 g, 98%) as a yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. concentrationthe filtrated concentrated

Sources & evidence

ORD record
ord-44085cc51e6d43888c44c36770e0978b
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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