Ammonia → 6-Methoxyisoquinolin-1-amine

HRID 1438141Notes

Reaction equation

HRID 1438141 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-a48a5e2c64bd44ab84c2cb801ef440f5
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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