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

HRID 418481Notes

Reaction equation

HRID 418481 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[NH2:15][C@H:16]([CH3:19])[CH2:17][OH:18].C(N(CC)CC)C.CO>>[OH:18][CH2:17][C@H:16]([N:15]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14])[CH3:19]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 59515694(R)-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-oneYield 40%

Conditions

Temperature
88 °C

Procedure

A 250 mL round bottom flask was charged with 5-nitro-isochromen-1-one (40 g, 0.2 mol), (2R)-2-Aminopropan-1-ol (18 g, 0.24 mol), triethylamine (100 mL, 0.7 mol) and methanol (500 mL, 10 mol) and the reaction heated at 88° C. for 1.5 hours. The product precipitated out upon cooling the reaction and was filtered to afford the product as a yellow solid. (17.3 g, 40% yield).

Workup

  1. customThe product precipitated out
  2. temperatureupon cooling
  3. customthe reaction
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-276a6ba1188e448898e2a550dfa68f05
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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