Ethylene Glycol → 6-Nitro-1,2-dihydroisoquinolin-1-one

HRID 708797Notes

Reaction equation

HRID 708797 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:6]=1[C:7](OC)=[O:8].N.C(O)CO>>[N+:15]([C:13]1[CH:14]=[C:5]2[C:6](=[CH:11][CH:12]=1)[C:7](=[O:8])[NH:2][CH:3]=[CH:4]2)([O-:17])=[O:16]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 87664981(E)-Methyl 2-(2-(dimethylamino)vinyl)-4-nitrobenzoate

Product 1

HCID 707009796-Nitro-1,2-dihydroisoquinolin-1-oneYield 85%

Conditions

Temperature
140 °C

Procedure

To Intermediate 3B (1.54 g, 6.15 mmol) in a microwave tube was added 8.0 N ammonia in ethylene glycol (7.69 mL, 61.5 mmol). The tube was placed in microwave and heated at 140° C. for 30 min. The reaction mixture was triturated with EtOAc, stored at 0° C. over night. The precipitate was collected to give Intermediate 3C (0.995 g, 5.23 mmol, 85% yield) as a brown solid. The filtrate was washed with water. The organic layer was dried over sodium sulfate. After evaporation of solvent, the crude was triturated with EtOAc to give additional product. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.35 (br. s., 1H) 8.63 (d, J=2.20 Hz, 1H) 8.39 (d, J=8.79 Hz, 1H) 8.19 (dd, J=8.79, 2.20 Hz, 1H) 7.36 (d, J=7.03 Hz, 1H) 6.82 (d, 1H); MS (ESI) m/z: 191.1 (M+H)+.

Workup

  1. customThe reaction mixture was triturated with EtOAc
  2. waitstored at 0° C. over night
  3. customThe precipitate was collected

Sources & evidence

ORD record
ord-233ece1c319746318debc57332713bfd
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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