Ammonium formate → HCID 18951360, compound

HRID 1492694Notes

Reaction equation

HRID 1492694 reaction equation
[OH:1][C:2]1[C:7]2=[CH:8][C:9]3[C:14]([N:6]2[CH2:5][CH2:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=[CH:11][CH:10]=3.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:1][CH:2]1[C:7]2=[CH:8][C:9]3[C:14]([N:6]2[CH2:5][CH2:4][CH:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54678585HCID 54678585, compound

Product 1

HCID 18951360HCID 18951360, compoundYield 96,413.297%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 18 g (0.07 mmol) of ethyl 6,7-dihydro-9-hydroxypyrido[1,2-a]indole-8-carboxylate and 13.3 g of 0.21 mmol) of ammonium formate in 300 ml of ethanol is treated under a nitrogen atmosphere with 2.2 g of 10% palladium/charcoal and heated to reflux temperature for 4 hours. The resulting suspension is cooled to room temperature, filtered and the solid is washed with 50 ml of ethanol and twice with 50 ml of methylene chloride, each time. Then, the filtrate and the washings are evaporated and the residue is taken up in a mixture of ethyl acetate and water (5:4, total 450 ml). The organic phase is washed with 100 ml of sodium chloride solution, dried over anhydrous sodium sulfate and evaporated to dryness. In this manner, there are obtained 17.5 g (96%) of ethyl 6,7,8,9-tetrahydro-9-hydroxypyrido[1,2-a]indole-8-carboxylate as a beige solid, m.p. 116°-120° C.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 4 hours
  3. filtrationfiltered
  4. washthe solid is washed with 50 ml of ethanol and twice with 50 ml of methylene chloride
  5. customThen, the filtrate and the washings are evaporated
  6. additionthe residue is taken up in a mixture of ethyl acetate and water (5:4, total 450 ml)
  7. washThe organic phase is washed with 100 ml of sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-45fd872fff20495c8051ea18823aa94e
Source dataset
uspto-grants-1994_12
Patent number
US05374727

Reaction notes

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