HCID 13800227, compound → N-(2-aminoethyl)-3-hydroxy-5-chloropyridine-2-carboxamide hydrochloride

HRID 34942Notes

Reaction equation

HRID 34942 reaction equation
C([O:8][C:9]1[C:10]([C:16]([NH:18][CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)=[O:17])=[N:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O>[ClH:15].[NH2:21][CH2:20][CH2:19][NH:18][C:16]([C:10]1[C:9]([OH:8])=[CH:14][C:13]([Cl:15])=[CH:12][N:11]=1)=[O:17]

Participants

3

Reactant 1

HCID 13800227HCID 13800227, compound

Product 1

HCID 13800268N-(2-aminoethyl)-3-hydroxy-5-chloropyridine-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.95 g of t-butyl [2-(3-benzyloxy-5-chloropyridine-2-carboxamido)ethyl]carbamate, m.p. 130°-133°, in 30 ml of trifluoroacetic acid was stirred at 50° for 7 hours. The mixture was thereafter evaporated to dryness on a rotary evaporator, the residue was dissolved in methanol and the solution was treated with hydrogen chloride in methanol (6N). After recrystallization from methanol there was obtained N-(2-aminoethyl)-3-hydroxy-5-chloropyridine-2-carboxamide hydrochloride, m.p. 220°-223°.

Workup

  1. customThe mixture was thereafter evaporated to dryness on a rotary evaporator
  2. dissolutionthe residue was dissolved in methanol
  3. additionthe solution was treated with hydrogen chloride in methanol (6N)
  4. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-d4a2c58271434edd92c7024eaef5c1a7
Source dataset
uspto-grants-1988_08
Patent number
US04764522

Reaction notes

Loading…