Methanol → (R)-6-Chloro-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one

HRID 418498Notes

Reaction equation

HRID 418498 reaction equation
[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[CH:6]=[CH:5]2.[NH2:16][C@H:17]([CH3:20])[CH2:18][OH:19].C(N(CC)CC)C.CO>>[Cl:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:16]([C@H:17]([CH3:20])[CH2:18][OH:19])[CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 595157256-Chloro-5-nitro-1H-isochromen-1-one

Product 1

HCID 59515901(R)-6-Chloro-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one

Conditions

Temperature
100 °C

Procedure

A microwave vial was charged with 6-chloro-5-nitro-1H-isochromen-1-one (80.0 mg, 0.000355 mol), (2R)-2-aminopropan-1-ol (29 mg, 0.00039 mol), triethylamine (0.15 mL, 0.0011 mol) and methanol (4 mL, 0.1 mol), and heated under microwave irradiation at 100° C. for 30 minutes. the solvent was removed under reduced pressure and the residue purified by flash chromatography to afford the desired product as a light yellow solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-efa0e4624c484d9198d3abb0392db6bf
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

Loading…