Sodium hydride → t-butyl N-[2-nitro-5-(2-pyrrolidinophenoxy)phenyl]-N-methylcarbamate

HRID 2303862Notes

Reaction equation

HRID 2303862 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:14]1[CH:15]=[CH:16][C:17]([N+:29]([O-:31])=[O:30])=[C:18]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=1.[H-].[Na+]>CN(C)C=O>[N+:29]([C:17]1[CH:16]=[CH:15][C:14]([O:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[CH:19][C:18]=1[N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27348452-(Pyrrolidin-1-yl)phenolHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18461415t-butyl N-[2-nitro-5-(2-pyrrolidinophenoxy)phenyl]-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to that described in Reference Example 27, a reaction was carried out using 2-pyrrolidinophenol (1.88 g), t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (3.34 g), sodium hydride (55 wt. %, 0.52 g) and anhydrous N,N-dimethylformamide (22 ml) and the reaction mixture was purified to afford t-butyl N-[2-nitro-5-(2-pyrrolidinophenoxy)phenyl]-N-methylcarbamate, of which Rf value was 0.25 in thin layer chromatography on a silica gel plate using c-hexane/ethyl acetate=10/1. In a similar manner to that described in Reference Example 27, a reaction was carried out using this product, palladium on carbon (10%, 0.45 g) and toluene/methanol=7/3 (50 ml) and the reaction mixture was purified to give the title compound (3.0 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-179558f8fc5c428b9e06e524b63eda4e
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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