Formic Acid → HCID 20446688, compound

HRID 2417816Notes

Reaction equation

HRID 2417816 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:5][N:4]=1.[OH-].[NH4+].[CH:19](O)=[O:20]>>[CH:19]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:5][N:4]=1)=[O:20]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 14923Ammonium HydroxideHCID 15586480HCID 15586480, compound

Product 1

HCID 20446688HCID 20446688, compound

Procedure

2-Aminomethyl-5-(4-methoxycarbonylbutyl)pyridine (0.20 g) is heated at 90° in 0.6 ml of formic acid for 18 hours. The mixture is cooled to 0°, made basic with saturated ammonium hydroxide solution and extracted with methylene chloride (4×15 ml). Drying, filtration and evaporation of the extracts yields 2-(N-formylaminomethyl)-5-(4-methoxycarbonylbutyl)pyridine as an oil (IR 1720, 1675 cm-1) which is redissolved in 1 ml of toluene and heated at 90° for 18 hours with phosphorus oxychloride (0.166 g). Evaporation of excess phosphorus oxychloride with toluene, basification at 0° with saturated ammonium hydroxide solution, extraction with methylene chloride (4×15 ml) and drying over sodium sulfate yields an oil which is chromatographed (silica gel, ethyl acetate) to yield 6-(4-methoxycarbonylbutyl)-imidazo[1,5-a]pyridine; Rf=0.26; NMR (CDCl3) 3.58 (s, 3H), 6.45 (d, 1H), 7.25 (d, 1H), 7.38 (s, 1H), 7.62 (s, 1H), 7.94 (s, 1H); IR (CH2Cl2) 1730 cm-1.

Workup

  1. temperatureThe mixture is cooled to 0°
  2. extractionextracted with methylene chloride (4×15 ml)
  3. customDrying
  4. filtrationfiltration and evaporation of the extracts

Sources & evidence

ORD record
ord-9dcdfcc3e9cf40f4aacff99c38dd26ab
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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