2-Chloronicotinic acid → HCID 20032011, compound

HRID 231769Notes

Reaction equation

HRID 231769 reaction equation
[OH:1][CH:2]([CH2:11][OH:12])[CH2:3][N:4]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Cl[C:14]1[N:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>O1CCOCC1>[OH:1][CH:2]([CH2:11][OH:12])[CH2:3][N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:14]2[N:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 17913078HCID 17913078, compound

Product 1

HCID 20032011HCID 20032011, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Grams 5 of 1-(2,3-dihydroxypropyl)homopiperazine and 2.25 g of 2-chloronicotinic acid in 50 ml dioxane were refluxed for 24 hours. The reaction mixture was evaporated to dryness and the residue was purified on column eluting with ethanol:ammonium hydroxyde (95:5). The fractions containing the product were dried and the residue, triturated with acetonitrile, gave 1.3 g of 2-[4-(2,3-dihydroxypropyl)homopiperazin-1-yl]nicotinic acid, melting at 70°-77° C. (with decomposition).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was purified on column
  3. washeluting with ethanol
  4. additionThe fractions containing the product
  5. customwere dried
  6. customthe residue, triturated with acetonitrile

Sources & evidence

ORD record
ord-1409139abb0748d1bf3b2ad1be0af28d
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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