Cyclopropylamine → HCID 21701954, compound

HRID 1596441Notes

Reaction equation

HRID 1596441 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:17])=[C:11]([CH:16]=1)[C:12](OC)=[O:13])#[N:6]>CS(C)=O.O>[CH:1]1([NH:4][C:12](=[O:13])[C:11]2[CH:16]=[C:7]([C:5]#[N:6])[CH:8]=[CH:9][C:10]=2[OH:17])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 10583428Methyl 5-cyano-2-hydroxybenzoate

Product 1

HCID 21701954HCID 21701954, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopropyl amine (14.3 g) and Na (100 mg) were added to a solution of methyl 5-cyano-2-hydroxybenzoate (10.0 g; from step (b) above) in DMSO (40 mL). The reaction mixture was heated at 80° C. in a sealed steel vessel overnight, diluted with H2O, acidified and extracted with EtOAc giving the sub-title compound (11.0 g), after concentration of the organic layer.

Workup

  1. extractionextracted with EtOAc giving the sub-title compound (11.0 g)

Sources & evidence

ORD record
ord-c741ba9118614520b62e5b2d31c9808d
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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