Sodium Hydroxide → 4-Amino-cinnamamide

HRID 866747Notes

Reaction equation

HRID 866747 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][C:8]#[N:9])=[CH:4][CH:3]=1.[OH-:12].[Na+]>O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([NH2:9])=[O:12])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 545249384-Aminocinnamonitrile

Product 1

HCID 540135574-Amino-cinnamamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

72 parts of 4-amino-cinnamonitrile are gradually added to 85 parts of 66° Be sulphuric acid diluted by 15 parts of water. The temperature rises of itself to 100°-105° C. It is maintained up to the end of the addition, then heated for 50 minutes at 100°-105° C., cooled to 20° C. and run on to 100 parts of water and 200 parts of ice. The product is neutralised by adding 170 parts of a 35° Be solution of sodium hydroxide, the temperature being maintained at 10°-20° C. and the solid is then filtered off and dried. 56 parts of 4-amino-cinnamamide are thus obtained. It is recrystallised from 400 parts of monochlorobenzene, M.p. 200° C.

Workup

  1. customrises of itself to 100°-105° C
  2. temperatureIt is maintained up to the end of the addition
  3. temperatureheated for 50 minutes at 100°-105° C.
  4. temperaturethe temperature being maintained at 10°-20° C.
  5. filtrationthe solid is then filtered off
  6. customdried

Sources & evidence

ORD record
ord-a5bc7c115e7b4d2e93b5f271a3b494f1
Source dataset
uspto-grants-1978_07
Patent number
US04101543

Reaction notes

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