Tert-butyl 2-(2-hydroxybenzamido)propylcarbamate → N-(1-aminopropan-2-yl)-2-hydroxybenzamide

HRID 1027657Notes

Reaction equation

HRID 1027657 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH:7]([CH3:17])[CH2:8][NH:9]C(=O)OC(C)(C)C)=[O:5]>Cl.CO>[NH2:9][CH2:8][CH:7]([NH:6][C:4](=[O:5])[C:3]1[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=1[OH:1])[CH3:17]

Participants

3

Reactant 1

HCID 67493246Tert-butyl 2-(2-hydroxybenzamido)propylcarbamate

Product 1

HCID 63732371N-(1-aminopropan-2-yl)-2-hydroxybenzamideYield 113.6%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of tert-butyl 2-(2-hydroxybenzamido)propylcarbamate (2.4 g, 8.16 mmol) in saturated HCl-MeOH (50 mL) was stirred (RT, 2 h) and concentrated under reduced pressure to afford N-(1-aminopropan-2-yl)-2-hydroxybenzamide (1.8 g, 96%) as a white solid. Mass calculated for C10H14N2O2=194.23. found: [M+H]+=195.2.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89ba34afb87443afa15729dd0258c11c
Source dataset
uspto-grants-2014_05
Patent number
US08735379B2

Reaction notes

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