Methylhydrazine → HCID 135982274, compound

HRID 887010Notes

Reaction equation

HRID 887010 reaction equation
O[CH:2]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16]C)[CH:12]=2)[C:7]1=O)[C:3](O)=[O:4].[CH3:19][NH:20][NH2:21].B(Br)(Br)Br>CC(O)C>[OH:16][C:11]1[CH:10]=[CH:9][C:8]2[C:7]3[C:6](=[CH:2][C:3](=[O:4])[N:20]([CH3:19])[N:21]=3)[CH2:15][CH2:14][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 25134Boron tribromideHCID 59651944HCID 59651944, compound

Product 1

HCID 135982274HCID 135982274, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of the product from step 1 (700 mg, 2.8 mmol) and N-methylhydrazine (0.3 mL) in 2-propanol (10 mL) was heated to reflux 18 h. The solvent was removed under vacuum and the solid was triturated with methanol (2 mL), collected and then suspended in methylene chloride (2 mL) at 0° C. BBr3 (10 mL of 1M solution in DCM, 10 mmol) was slowly added dropwise and the ice bath removed. After 3 h at ambient temperature, saturated NH4Cl solution (10 mL) was added. The DCM was removed under vacuum and the resulting slurry was carefully neutralized with saturated NaHCO3 solution and washed with water. The solids were collected to afford 8-hydroxy-2-methyl-5,6-dihydro-2H-benzo[h]cinnolin-3-one (175 mg, 27%) as a white solid; m p>300° C. MS m/z 229 (M+H).

Workup

  1. temperatureto reflux 18 h
  2. customThe solvent was removed under vacuum
  3. customthe solid was triturated with methanol (2 mL)
  4. customcollected
  5. customsuspended in methylene chloride (2 mL) at 0° C
  6. customthe ice bath removed
  7. additionsaturated NH4Cl solution (10 mL) was added
  8. customThe DCM was removed under vacuum
  9. washwashed with water
  10. customThe solids were collected

Sources & evidence

ORD record
ord-fc379e86c22f4791b1b30234672d246c
Source dataset
uspto-grants-2012_08
Patent number
US08247414B2

Reaction notes

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