Methylhydrazine → HCID 66917791, compound

HRID 1818007Notes

Reaction equation

HRID 1818007 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:3]=1[C:4]#[N:5].CN(C)C(=O)C.[CH3:27][NH:28][NH2:29]>O>[CH3:27][N:28]1[C:2]2[C:3](=[C:6]([O:10][C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]=3)[CH:7]=[CH:8][CH:9]=2)[C:4]([NH2:5])=[N:29]1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 31374DimethylacetamideHCID 55374169HCID 55374169, compound

Product 1

HCID 66917791HCID 66917791, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a 20 mL vial containing 2-fluoro-6-(naphthalen-2-yloxy)-benzonitrile (966 mg, 3.67 mmol) and a magnetic stir bar was added anhydrous N,N-dimethylacetamide and the mixture was stirred until solution was achieved. Methyl hydrazine (390 uL, 7.34 mmol) was added, the vial was capped, the reaction mixture was placed in an oil bath at 120° C. and stirred at that temperature overnight. The reaction mixture was heated at 130° C. for an additional 3 h. The cooled reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×30 mL). The combined organics were washed with water (3×15 mL), dried (Na2SO4), filtered and concentrated to give 1.03 g of a tan solid. This residue was purified via flash chromatography on silica gel (120 g) utilizing CH2Cl2 and then 9:1 CH2Cl2/EtOAc as eluent to give 770 mg of I-190 an off-white solid. This material was deemed of sufficient purity to be utilized in subsequent reactions. 1H NMR, MS.

Workup

  1. customthe vial was capped
  2. customthe reaction mixture was placed in an oil bath at 120° C.
  3. stirringstirred at that temperature overnight
  4. customThe cooled reaction mixture
  5. extractionextracted with EtOAc (2×30 mL)
  6. washThe combined organics were washed with water (3×15 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8a16691dbe634fa1a00fd2044518293b
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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