Aniline → HCID 19026977, compound

HRID 1032950Notes

Reaction equation

HRID 1032950 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][O:13][CH3:14])[CH:6]=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na].Cl.CO.C(=O)([O-])O.[Na+]>CO.O>[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][O:13][CH3:14])[CH2:6][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 190269753-Dimethylamino-4-methoxymethoxybenzaldehydeHCID 21893726Hydrochloride methanol

Product 1

HCID 19026977HCID 19026977, compoundYield 120.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of Compound A (1.71 g, 8.17 mmol) in methanol (80 ml) was added dropwise aniline (1.49 ml, 16.3 mmol), and the mixture was stirred at room temperature for 15 minutes. Thereto was added sodium cianoborohydride (1.62 g, 24.5 mmol) by portions. The pH of the reaction mixture was adjusted to 7 by the addition of hydrochloric acid-methanol. After being stirred for 1 hour, the reaction mixture was poured into water and basified with sodium hydrogencarbonate. The mixture was extracted with ethyl acetate, washed with water, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated to give the title compound (1) (2.82 g) in quantative yield.

Workup

  1. stirringAfter being stirred for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4d6db1fc7c0a42788433c7fdfac6f992
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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