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

HRID 418515Notes

Reaction equation

HRID 418515 reaction equation
[CH3:1][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>>[OH:19][CH2:18][C@H:17]([N:16]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[C:3]=2[N+:13]([O-:15])=[O:14])[C:8]1=[O:12])[CH3:20]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 595157846-Methyl-5-nitro-1H-isochromen-1-one

Product 1

HCID 59515931(R)-2-(1-hydroxypropan-2-yl)-6-methyl-5-nitroisoquinolin-1(2H)-one

Conditions

Temperature
80 °C

Procedure

A round bottom flask was charged with 6-methyl-5-nitro-1H-isochromen-1-one (260.00 mg, 0.0012673 mol), (2R)-2-aminopropan-1-ol (143 mg, 0.00190 mol), triethylamine (1.6 L, 0.011 mol) and methanol (5 mL, 0.1 mol) and the reaction was heated at 80° C. overnight. The solvent was removed under reduced pressure and the residue purified by flash chromatography to afford the 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-96915e0dd6144016b1994a3f5bd4d136
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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