Methanol → 1-Methoxy-5-nitroisoquinoline

HRID 1645912

Reaction equation

HRID 1645912 reaction equation
[Na].Cl[C:3]1[C:12]2[C:7](=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[CH3:16][OH:17]>>[CH3:16][O:17][C:3]1[C:12]2[C:7](=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4597741-Chloro-5-nitroisoquinolineHCID 5360545Sodium

Product 1

HCID 8306811-Methoxy-5-nitroisoquinoline

Procedure

To a solution of 1.0 g of sodium (43.4 mmol) in methanol was added 1.42 g (6.8 mmol) of 1-chloro-5-nitroisoquinoline. The mixture was heated under reflux for three hours, cooled, and concentrated. The residue was partitioned between water and methylene chloride, dried, and filtered through SiO2. The filtrate was concentrated to give 1.3 g of the 1-methoxy-5-nitroisoquinoline. This material was suspended in 150 ml of methanol, 0.3 g of 5% Pd-C was added, and the mixture was hydrogenated at room temperature for 18 hours. The mixture was filtered and concentrated. The residue was crystallized from ether/hexane to give 0.32 g (27%) of the desired product; mp 53°-57°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for three hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was partitioned between water and methylene chloride
  6. customdried
  7. filtrationfiltered through SiO2
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d5db6b2f2661446bab1d2b4b9d2e616c
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Linked notes

Loading…