Ammonium Hydroxide → 8-methoxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one

HRID 2042641Notes

Reaction equation

HRID 2042641 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.O.[C:15]([OH:19])(=O)[CH:16]=O.[NH4+:20].[OH-].O.[NH2:23]N.C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9]3[C:8]([CH2:7][CH2:6][C:5]=2[CH:4]=1)=[N:23][NH:20][C:15](=[O:19])[CH:16]=3

Participants

8

Reactant 5

HCID 14923Ammonium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 516892Sodium BicarbonateHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 596519778-methoxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a 50 mL round bottom flask, 6-methoxy-3,4-dihydro-1H-naphthalen-2-one (1.0 g, 5.68 mmol), and glyoxylic acid monohydrate (523 mg, 5.68 mmol), in acetic acid (10 mL) was heated to reflux 3 h. The reaction was cooled and diluted with water (20 mL). The mixture was basified to pH 8 with NH4OH and then hydrazine monohydrate (0.55 mL, 11.4 mmol) was added. The reaction was heated to reflux 2 h. The reaction was cooled and re-basified with NaHCO3, then extracted with methylene chloride three times. The organics were dried over MgSO4, and the solvents were removed under vacuum to produce 1.1 g (85%). mp dec. 270° C. MS m/z=229 (M+H).

Workup

  1. temperatureto reflux 3 h
  2. temperatureThe reaction was cooled
  3. temperatureThe reaction was heated
  4. temperatureto reflux 2 h
  5. extractionextracted with methylene chloride three times
  6. dry with materialThe organics were dried over MgSO4
  7. customthe solvents were removed under vacuum
  8. customto produce 1.1 g (85%)
  9. custom270° C

Sources & evidence

ORD record
ord-3ae0d64e676c4fd3842418b495a03b61
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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