Hydroxylamine → 5-[5-(Hydroxycarbamoyl)pentyl]-imidazo[1,5-a]-pyridine

HRID 2417834Notes

Reaction equation

HRID 2417834 reaction equation
[NH2:1][OH:2].C[O:4][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[N:17]2[CH:18]=[N:19][CH:20]=[C:16]2[CH:15]=[CH:14][CH:13]=1)=O>CO>[OH:2][NH:1][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[N:17]2[CH:18]=[N:19][CH:20]=[C:16]2[CH:15]=[CH:14][CH:13]=1)=[O:4]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 233218845-(5-Methoxycarbonylpentyl)imidazo[1,5-a]pyridine

Product 1

HCID 133736345-[5-(Hydroxycarbamoyl)pentyl]-imidazo[1,5-a]-pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of hydroxylamine (from 2.06 g of hydroxylamine hydrochloride and 2.02 g of sodium hydroxide) and 5-(5-methoxycarbonylpentyl)imidazo[1,5-a]pyridine (6.08 g) in 25 ml of methanol is allowed to stand at room temperature for 20 hours. The methanol is evaporated and the residue is taken up in 5 ml of water and adjusted to pH=7. The resulting oil crystallizes and the solid is collected, yielding 5-[5-(hydroxycarbamoyl)pentyl]-imidazo[1,5-a]-pyridine, m.p. 138°-140°.

Workup

  1. customThe methanol is evaporated
  2. customThe resulting oil crystallizes
  3. customthe solid is collected

Sources & evidence

ORD record
ord-ba7f7f75a787447596fc5eacff0115a7
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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