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

HRID 1161273Notes

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

Reactant 4

HCID 887Methanol

HCID 8471Triethylamine

HCID 80308(R)-(-)-2-Amino-1-propanol

HCID 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

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 subjected to microwaves at 100° C. for 30 minutes. The reaction went to completion with 10% of cyclized product in addition to the required product. The solvent was removed and the residue purified by flash chromatography to obtain the product as a light yellow solid. MS m/z=283.2 (M+H). 1H NMR (400 MHz; DMSO-d6) δ 8.43 (d, J=8.86 Hz, 1H), 7.80 (d, J=8.86 Hz, 1H), 7.75 (d, J=7.98 Hz, 1H), 6.36 (d, J=7.09 Hz, 1H), 5.03-4.86 (m, 2H), 3.63-3.52 (m, 2H), 1.30 (d, J=7.0 Hz, 3H).

Sources & evidence

ORD record: ord-47996f9c26474101a0270ff945813398
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816371B2

Reaction notes

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