Dimethylformamide dimethyl acetal → HCID 178526359, compound

HRID 876824Notes

Reaction equation

HRID 876824 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1.C[N:11]([CH:13](OC)OC)C.N[OH:19].Cl>CC(O)C>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][CH:13]=[N:11][OH:19])[CH:4]=1

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 443297Hydroxyamine hydrochlorideHCID 451082084-(Chloromethyl)pyridin-2-amine

Product 1

HCID 178526359HCID 178526359, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(chloromethyl)pyridin-2-amine (4-1) (1.56 g, 8.7 mmol) in propan-2-ol (15 mL) was added DMF-DMA (1.56 mL, 11.3 mmol) at room temperature under N2. The reaction mixture was heated to 90° C. for 3 h. After cooled to 50° C., the mixture was treated with NH2OH.HCl (0.781 g, 11.3 mmol), then stirred at 50° C. overnight. After cooled to room temperature, the mixture was concentrated and purified by chromatography on silica gel to afford the title compound (820 mg). MS (m/z): 186 (M+1)+.

Workup

  1. temperatureAfter cooled to 50° C.
  2. temperatureAfter cooled to room temperature
  3. concentrationthe mixture was concentrated
  4. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-807fcd1429d04fc2b39b3fa6cf263654
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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