Potassium Carbonate → HCID 13649488, compound

HRID 1982383Notes

Reaction equation

HRID 1982383 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([O:14][CH3:15])=[O:13])([O-])=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.[Pd]>[NH2:1][C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 13649487HCID 13649487, compound

Product 1

HCID 13649488HCID 13649488, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1117 g methyl 1-(2-nitrobenzyl)-pyrrole-2-carboxylate in 1117 mL of tetrahydrofuran, 458 g of potassium carbonate in 840 mL of water and 19 g of 5% palladium on carbon is stirred and heated to a temperature of 60°. The heat is removed and a solution of 1876 g of sodium hypophosphite hydrate in 3725 mL of water is added slowly over a period of one hour. The refluxing is controlled by the rate of the addition. When the addition is complete the mixture is refluxed, with stirring, for 2 hours. After stirring at room temperature for 5 hours, the reaction mixture is allowed to stand overnight. Methylene chloride (4 L) is added, the mixture is stirred for 3 hours and then filtered through filter-cel. The methylene chloride layer is separated and dried over magnesium sulfate. The magnesium sulfate is filtered off and the filtrate is concentrated to dryness to give a residue which is dried at 40°-50° and high vacuum to yield methyl 1-(2-aminobenzyl)-pyrrole-2-carboxylate, m.p. 95°-97°.

Workup

  1. temperatureheated to a temperature of 60°
  2. customThe heat is removed
  3. additiona solution of 1876 g of sodium hypophosphite hydrate in 3725 mL of water is added slowly over a period of one hour
  4. additionThe refluxing is controlled by the rate of the addition
  5. additionWhen the addition
  6. temperatureis refluxed
  7. stirringAfter stirring at room temperature for 5 hours
  8. waitto stand overnight
  9. additionMethylene chloride (4 L) is added
  10. stirringthe mixture is stirred for 3 hours
  11. filtrationfiltered
  12. filtrationthrough filter-cel
  13. customThe methylene chloride layer is separated
  14. dry with materialdried over magnesium sulfate
  15. filtrationThe magnesium sulfate is filtered off
  16. concentrationthe filtrate is concentrated to dryness
  17. customto give a residue which
  18. customis dried at 40°-50°

Sources & evidence

ORD record
ord-9a688a46b88749e7a03ad495c59c57dc
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

Loading…