Pyridine → (R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 1161274Notes

Reaction equation

HRID 1161274 reaction equation
[Cl:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C@H:13]([CH3:16])[CH2:14][OH:15])[CH:6]=[CH:5]2.[C:20](OC(=O)C)(=[O:22])[CH3:21].N1C=CC=CC=1.C(Cl)Cl>>[C:20]([O:15][CH2:14][C@H:13]([N:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=2[N+:17]([O-:19])=[O:18])[C:8]1=[O:12])[CH3:16])(=[O:22])[CH3:21]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 59515901(R)-6-Chloro-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one

Product 1

HCID 59515821(R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Conditions

Temperature
45 °C

Procedure

A mixture of (R)-6-chloro-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one (750.0 mg, 0.002653 mol), acetic anhydride (0.325 mL, 0.00345 mol), pyridine (0.322 mL, 0.00398 mol) and methylene chloride (20 mL, 0.3 mol) was heated at 45° C. over night. The solvent was removed under reduced pressure and dried to get pure product as thick yellow oil. MS m/z=325.4 (M+H). 1H NMR (400 MHz; DMSO) δ 8.42 (d, J=8.61 Hz, 1H), 7.47 (d, J=8.61 Hz, 1H), 7.23 (d, J=8.6 Hz, 1H), 6.29 (d, J=8.03 Hz, 1H), 5.34-5.29 (m, 1H), 4.28-4.20 (m, 2H), 1.94 (s, 3H), 1.40 (d, J=6.96 Hz, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customdried
  3. customto get pure product as thick yellow oil

Sources & evidence

ORD record
ord-c06731829077444e905328123809ffb1
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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