Methylhydrazine → HCID 135982274, compound

HRID 221810Notes

Reaction equation

HRID 221810 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-f0b05681c29d4449a7deb62a9a8ae01b
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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