Chlorosuccinimide → HCID 68737846, compound

HRID 1628532Notes

Reaction equation

HRID 1628532 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:18]N1C(=O)CCC1=O>ClCCl>[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:18])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 68738220HCID 68738220, compound

Product 1

HCID 68737846HCID 68737846, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 3-amino-2-[(4-hydroxybutyl)amino]benzoate (29.8 g, 125 mmol) in dichloromethane (500 mL) was added N-chlorosuccinimide (33.3 g, 250 mmol) at room temperature. After 4 h, the reaction mixture was quenched with aqueous sodium hydrogen carbonate and purified by flash column chromatography on silica gel eluting with a 30% ethyl acetate/n-hexane mixture to give the title compound as a pale red solid (5.81 g, 21.3 mmol, 17%).

Workup

  1. customthe reaction mixture was quenched with aqueous sodium hydrogen carbonate
  2. custompurified by flash column chromatography on silica gel eluting with a 30% ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-e3b3a23871024d9dbd82cd024e4022b2
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

Loading…