Ammonia → HCID 22320827, compound

HRID 498135Notes

Reaction equation

HRID 498135 reaction equation
[CH:1]([N:4]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[C:5](=[O:10])/[CH:6]=[C:7](\[NH2:9])/[CH3:8])([CH3:3])[CH3:2].N.[H][H]>[Ni].CO>[NH2:9][CH:7]([CH3:8])[CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 222Ammonia2×HCID 69738282HCID 69738282, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22320827HCID 22320827, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

(Z)-3-Aminobut-2-enoic acid N-isopropyl-N-[4-(phenylamino)phenyl]amide (13.9 g, 0.0449 mol) and Raney nickel (K0840 Ni B113W) (2.0 g) in methanol (140 g) were introduced into an autoclave. Ammonia (5.5 g, 0.3230 mol) was introduced in the course of 5 minutes. The temperature of the reaction mixture was 25° C. The pressure rose to 5 bar. After the introduction of ammonia, the reaction mixture was warmed to 80° C. (no further pressure rise). Hydrogen was injected at 80° C. until the pressure was 100 bar. The reaction mixture was heated to 110° C. and stirred at this temperature for 4.5 h. In the course of this, a pressure of 100 bar was maintained by continuous injection of hydrogen. The reaction mixture was cooled to 25° C. and the pressure was carefully let down. The reaction mixture was filtered off and the filtrate was concentrated to one half. The concentrate was treated with 1 g of active carbon, stirred for 1 h, filtered and concentrated to dryness. 12.8 g of crude product were obtained, which was melted at 175° C. The melt could be crystallized on an aluminium foil. 11.1 g of 3-amino-N-isopropyl-N-[4-(phenylamino)phenyl]butyramide (79.3%) were obtained.

Workup

  1. customwas 25° C
  2. customwas injected at 80° C. until the pressure
  3. temperatureThe reaction mixture was cooled to 25° C.
  4. filtrationThe reaction mixture was filtered off
  5. concentrationthe filtrate was concentrated to one half
  6. additionThe concentrate was treated with 1 g of active carbon
  7. stirringstirred for 1 h
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. custom12.8 g of crude product were obtained
  11. customThe melt could be crystallized on an aluminium foil

Sources & evidence

ORD record
ord-93a71ad54a87496fa9ca45052e184077
Source dataset
uspto-grants-2005_09
Patent number
US06949677B2

Reaction notes

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