Formic Acid → Ammonia

HRID 1593951Notes

Reaction equation

HRID 1593951 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[N:10][C:9]([N:12]3[CH2:17][C@@H:16]4[CH2:18][C@H:13]3[CH2:14][NH:15]4)=[CH:8][CH:7]=2)=[CH:2]1.[CH:19](O)=O.C=O>>[NH3:10].[CH3:19][N:15]1[CH2:14][C@@H:13]2[CH2:18][C@H:16]1[CH2:17][N:12]2[C:9]1[N:10]=[N:11][C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 69415001HCID 69415001, compound

Product 2

HCID 222AmmoniaHCID 69415147HCID 69415147, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[6-(3-thienyl)-3-pyridazinyl]-(1S,4S)-(+)-2,5-diazabicyclo-[2.2.1]-heptane (0.21 g, 0.81 mmol), formic acid (0.92 ml, 24.4 mmol) and formaldehyde (0.68 ml, 24.4 mmol) was stirred at 100° C. for 6 hours. The mixture was evaporated. Aqueous sodium hydroxide (30 ml, 1 M) was added followed by extraction with ethyl acetate (3×30 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 0.15 g, 77%.

Workup

  1. customThe mixture was evaporated
  2. additionAqueous sodium hydroxide (30 ml, 1 M) was added
  3. extractionfollowed by extraction with ethyl acetate (3×30 ml)

Sources & evidence

ORD record
ord-c927d29dce3c46799b408f45d75f1228
Source dataset
uspto-grants-2007_11
Patent number
US07300933B2

Reaction notes

Loading…