Pyridine → HCID 178464036, compound

HRID 1390016Notes

Reaction equation

HRID 1390016 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH2:5][NH:6][C:7]1[C:12]([NH2:13])=[CH:11][CH:10]=[C:9]([Cl:14])[N:8]=1)[CH3:2].N1C=CC=CC=1.Cl[C:24](OCC)=[O:25]>O1CCOCC1>[CH2:15]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:7]2[N:8]=[C:9]([Cl:14])[CH:10]=[CH:11][C:12]=2[N:13]=[C:24]1[OH:25])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 202947442-(2-Diethylaminoethylamino)-3-amino-6-chloropyridine

Product 1

HCID 178464036HCID 178464036, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The solution of 80 grams of 2-(2-diethylaminoethylamino)-3-amino-6-chloropyridine in 900 ml of dioxane was treated with stirring with 32 ml of pyridine and 36.6 ml of ethyl chloroformate and stirred for one hour. The product precipitating thereby was washed with water and dried (2-(2-diethylaminoethylamino)-3-carbethoxy-amino-6-chloropyridine, M.P. 205°-206° C.) and subsequently melted with occasional stirring and held for 3 hours at 190°-210° C. After cooling the solidified melt was recrystallized from methanol under the addition of activated carbon and isopropanolic H Cl. M.P. of the hydrochloride 252°-254° C.; Yield 52.8 grams.

Workup

  1. customThe product precipitating
  2. washthereby was washed with water
  3. dry with materialdried (2-(2-diethylaminoethylamino)-3-carbethoxy-amino-6-chloropyridine, M.P. 205°-206° C.)
  4. stirringwith occasional stirring
  5. waitheld for 3 hours at 190°-210° C
  6. temperatureAfter cooling the solidified melt
  7. customwas recrystallized from methanol under the addition of activated carbon and isopropanolic H Cl
  8. customM.P. of the hydrochloride 252°-254° C.

Sources & evidence

ORD record
ord-2ff7e962a7bd4016a3920dcb75a0c7cb
Source dataset
uspto-grants-1981_01
Patent number
US04247556

Reaction notes

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