Hydrochloric Acid → HCID 86743917, compound

HRID 1650652Notes

Reaction equation

HRID 1650652 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[N:15]([O-])=O.[Na+].[CH2:19]([NH:22][C:23](=[O:27])[CH2:24][C:25]#[N:26])[CH2:20][CH3:21].C([O-])(=O)C.[Na+]>CC(O)=O.O.C(O)C>[C:25]([C:24](=[N:15][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:23]([NH:22][CH2:19][CH2:20][CH3:21])=[O:27])#[N:26]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 70152-AminobiphenylHCID 517045Sodium AcetateHCID 44299652-cyano-N-propylacetamideHCID 23668193Sodium Nitrite

Product 1

HCID 86743917HCID 86743917, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent4×

Procedure

To a solution of 2-aminobiphenyl (10.16 g) in HOAc (36 ml) was added water (18 ml) and concentrated hydrochloric acid (18 ml). The solution was cooled to -15° with stirring. To this mixture was added dropwise a solution of sodium nitrite (4.36 g) in water (18 ml), maintaining the internal temperature below -5°. The resulting clear purple solution was stirred an additional 10 min at -10°, and was then added to a solution of N-propyl-2-cyanoacetamide (Prepared according to Shulka, J. S., et al., Journal of the Indian Chemical Society, (1978) 55:281-283.) (9.08 g) in water (400 ml)/ethanol (200 ml) containing sodium acetate (80 g) which had been chilled to -4°. This mixture was stirred mechanically at 0° for 6 hours before being allowed to warm to room temperature over a 15 hr. period. The mixture was then diluted with water (600 ml) and stirred. After 51/2 hours, the precipitated solid was collected by filtration and was washed with water and hexane. There was thus obtained 19.47 grams (>100% crude yield) of title product as a 5:1 ratio of Z:E isomers, m.p. 180°-184°; 1H NMR (CHCl3 -d, characteristic peaks of Z-isomer only): 0.948 (t, 3H), 1.53 (m, 2H), 3.20 (q, 2H), 6.04 (br.t, exchangeable, 1H), 7.20-7.29 (m, 2H), 7.37-7.54 (m, 6H), 7.76 (d. 1H), 13.96 (br.s, exchangeable, 1H) ppm.

Workup

  1. temperatureThe solution was cooled to -15°
  2. temperaturemaintaining the internal temperature below -5°
  3. stirringThe resulting clear purple solution was stirred an additional 10 min at -10°
  4. customPrepared
  5. temperaturehad been chilled to -4°
  6. stirringThis mixture was stirred mechanically at 0° for 6 hours
  7. stirringstirred
  8. filtrationAfter 51/2 hours, the precipitated solid was collected by filtration
  9. washwas washed with water and hexane

Sources & evidence

ORD record
ord-9ed10f7f869c4a67970c871a3100f803
Source dataset
uspto-grants-1990_05
Patent number
US04925844

Reaction notes

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