Nitric Acid → HCID 77058980, compound

HRID 1503881Notes

Reaction equation

HRID 1503881 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:6]2.C(OC(=O)C)(=O)C.[N+:27]([O-])([OH:29])=[O:28].C(=O)(O)[O-].[Na+]>[N+](C)([O-])=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:27]([O-:29])=[O:28])[CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 23377987tert-Butyl 6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 77058980HCID 77058980, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a solution of the product of Example 53D (2.46 g, 9.35 mmol) in nitromethane (30 mL) at −10° C. was added acetic anhydride (5.7 g, 56.1 mmol) and concentrated nitric acid (0.88 g, 14 mmol). After stirring for 3 hours, the mixture was adjusted to pH 7 with aqueous sodium bicarbonate solution and extracted with dichloromethane (2×100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash chromatography eluting with 5:1 hexane:ethyl acetate to give the title compound. MS: 309 (M+H+).

Workup

  1. extractionextracted with dichloromethane (2×100 mL)
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography
  6. washeluting with 5:1 hexane

Sources & evidence

ORD record
ord-6face495b7cf4676b8dcc7ccada4b86a
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

Loading…