Isonicotinamide → HCID 5108430, compound

HRID 1164706Notes

Reaction equation

HRID 1164706 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.N[CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=O>P(Cl)(Cl)(Cl)=O>[N:5]1[CH:6]=[CH:7][C:2]([C:1]2[O:8][C:12]3[C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:19][CH2:20][C:11]=3[N:9]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 15074IsonicotinamideHCID 4128902-Amino-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 5108430HCID 5108430, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

The isonicotinamide of 2-amino-1-tetralone (1.14 g, 0.00429 mole) was placed in 12 ml of phosphorus oxychloride (phosphoryl chloride) and refluxed for 19 hours. The amide dissolved during this period of time. The excess reagent was removed under vacuum. The residue was treated with 12 ml of ethanol and 5 ml of water. The mixture was made basic with 10% KOH. On cooling, the product precipitated and was filtered to give 0.77 g (72% yield) of the oxazole, mp 129°-130° C. 1H NMR(δ, CDCl3): 3.10, 4H, A2B2 ; 7.3-7.9, 4H, m; 8.93, 4H, A2B2.

Workup

  1. temperaturerefluxed for 19 hours
  2. customThe excess reagent was removed under vacuum
  3. additionThe residue was treated with 12 ml of ethanol and 5 ml of water
  4. temperatureOn cooling
  5. customthe product precipitated
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-88487ad428294ce88cf1a3df8b38a6ea
Source dataset
uspto-grants-1990_03
Patent number
USH0000753

Reaction notes

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