Formic Acid → HCID 13206170, compound

HRID 326130Notes

Reaction equation

HRID 326130 reaction equation
[NH2:1][CH2:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=[CH:5][N:4]=1.[OH-].[NH4+].[CH:19](O)=[O:20]>>[CH:19]([NH:1][CH2:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:20]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 14923Ammonium HydroxideHCID 13206171HCID 13206171, compound

Product 1

HCID 13206170HCID 13206170, compound

Procedure

A solution of 0.1 g of 2-aminomethyl-3-(4-methoxycarbonylbutyl)pyridine in 0.6 ml of formic acid is heated at 90° for 18 hours. The mixture is cooled to 0°, made basic with saturated ammonium hydroxide solution and extracted with methylene chloride (4×10 ml). Drying, filtration and evaporation of the extracts yields 2-(N-formylaminomethyl)-3-(4-methoxycarbonylbutyl)pyridine, melting at 43°-45° C. which is redissolved in 1 ml of toluene and heated at 90° for 17 hours with 75 mg of phosphorus oxychloride. 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 as an oil, 8-(4-methoxycarbonylbutyl)-imidazo[1,5-a]pyridine; Rf 0.29; NMR (CDCl3) 3.70 (s, 3 H), 6.50 (d, 2 H), 7.43 (s, 1 H), 7.83 (t, 1 H), 8.22 (s, 1 H); IR (CH2Cl2) 1725 cm-1.

Workup

  1. temperatureThe mixture is cooled to 0°
  2. extractionextracted with methylene chloride (4×10 ml)
  3. customDrying
  4. filtrationfiltration and evaporation of the extracts

Sources & evidence

ORD record
ord-5efa6d57a57f4a1eb232d4d0da58eea9
Source dataset
uspto-grants-1984_04
Patent number
US04444775

Reaction notes

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