Sodium Bicarbonate → HCID 90102721, compound

HRID 1052466Notes

Reaction equation

HRID 1052466 reaction equation
C[O:2][C:3]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].C(=O)(O)[O-].[Na+]>>[CH3:11][N:9]([CH3:10])[CH2:8][CH2:7][CH2:6][O:5][C:4]1[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:3]=1[OH:2]

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 60207431HCID 60207431, compound

Product 1

HCID 90102721HCID 90102721, compoundYield 44%

Procedure

3-(2-Methoxy-4-nitrophenoxy)-N,N-dimethylpropan-1-amine (480 mg, 1.89 mmol) was heated at 100° C. overnight in 3 ml of bromhydric acid (48% in water). Once at room temperature, 4% sodium bicarbonate solution was added and extracted with ethyl acetate. The organic phase was successively washed with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 0.22 mg (44% yield) of the title compound were obtained and used in the next synthetic step without further purification. Purity: 91%

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was successively washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-a315a8f0b5a04a819a75abdc434a0455
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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