Ammonia → HCID 86604951, compound

HRID 1611211Notes

Reaction equation

HRID 1611211 reaction equation
CN(C)/[C:3](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[CH:4]\[CH:5]=[C:6]([C:9]#[N:10])C#N.[NH3:28].O.[CH3:30]O>>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:3]2[N:10]=[CH:9][CH:6]=[CH:5][C:4]=2[C:30]#[N:28])=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 962WaterHCID 59062734HCID 59062734, compound

Product 1

HCID 86604951HCID 86604951, compoundYield 4.3%

Conditions

Temperature
120 °C

Procedure

To a cold (−78° C.) solution of 2-((2Z)-3-(dimethylamino)-3-{2-[(4-methoxybenzyl)oxy]phenyl}-2-propenylidene)malononitrile (1.26 g, 3.51 mmol) in MeOH was added liquid NH3, and the mixture was heated at 120° C. in a sealed tube overnight. After cooled to room temperature, the reaction mixture was poured into water and the resulting mixture was extracted with ethyl acetate. The separated organic phase was washed with brine, and dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel (hexane:ethyl acetate, 70:30) to give 2-amino-6-({2-[(4-methoxybenzyl)oxy]phenyl}nicotinonitrile (0.050 g, yield; 4.3%).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography on silica gel (hexane:ethyl acetate, 70:30)

Sources & evidence

ORD record
ord-c4c446e70bb84ebdb5099b8f752b78a4
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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