Ammonia → 6-Methoxyisoquinolin-1-amine

HRID 1438140Notes

Reaction equation

HRID 1438140 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH3:14]>C(O)CO.CO.[Cu-]=O>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([NH2:14])=[N:3][CH:4]=[CH:5]2

Participants

6

Reactant 2

HCID 222AmmoniaHCID 219010741-Chloro-6-methoxyisoquinoline

Product 1

HCID 155384096-Methoxyisoquinolin-1-amineYield 72%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A sealable tube was charged with 83E (770 mg, 3.98 mmol), copper (I) oxide (30 mg) and ˜12M NH3 in ethylene glycol (5 mL). The tube was sealed and the reaction was heated to 120° C. for 72 h. After cooling to rt, the reaction was diluted with methanol and was purified via preparative HPLC (MeOH/water/TFA) to provide 83F (832 mg, 72%). LC-MS: 175.23 (M+H)+.

Workup

  1. customThe tube was sealed
  2. temperatureAfter cooling to rt
  3. customwas purified via preparative HPLC (MeOH/water/TFA)

Sources & evidence

ORD record
ord-f019cba809c34a30a87b41a2e8dd43a5
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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