Oxalic Acid → HCID 86623000, compound

HRID 254874Notes

Reaction equation

HRID 254874 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH3:19][O:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[O:23][CH2:24][CH2:25][NH2:26].[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33]>CC(O)C>[CH3:19][O:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[O:23][CH2:24][CH2:25][NH:26][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18]=12.[C:31]([O-:36])(=[O:35])[C:32]([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 17130052-(2-Methoxyphenoxy)ethyl amineHCID 50207104-Oxiranylmethoxy-9H-carbazole

Product 1

HCID 86623000HCID 86623000, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A mixture of 4-(oxiran-2-ylmethoxy)-9H-carbazole (II) (25.0 g, 104.60 mmole) and 62.5 ml 2-propanol is heated to 70° C. to 80° C. To this 2-(2-methoxyphenoxy)ethylamine (III) (25.33 g, 151.67 mmole) is added in one lot. The temperature of reaction mass is raised to reflux (80° C. to 85° C.) and maintain at this reaction temperature for one hour. After that, this reaction mass is added to the pre-heated (80° C. to 85° C.) solution of oxalic acid (14.6 g) (162.13 mmole) in 2-propanol (287.5 ml) and continued the reflux for next one-hour, cooled to 50° C. to 55° C. and maintain for 1 hour. The product is filtered at the same temperature followed by three 33.5 ml wash with hot (50° C. to 55° C.) 2-propanol. The wet product dried at 60° C. to 65° C. for 6-8 hours or till constant weight gives 42.0 g of Carvedilol Oxalate (Yield 80.95%).

Workup

  1. temperatureis heated to 70° C. to 80° C
  2. customThe temperature of reaction mass
  3. temperatureis raised
  4. temperatureto reflux (80° C. to 85° C.)
  5. temperaturemaintain at this reaction temperature for one hour
  6. additionAfter that, this reaction mass is added to the
  7. temperaturereflux for next one-hour
  8. temperaturecooled to 50° C. to 55° C.
  9. temperaturemaintain for 1 hour
  10. filtrationThe product is filtered at the same temperature
  11. washwash with hot (50° C. to 55° C.) 2-propanol
  12. customThe wet product dried at 60° C. to 65° C. for 6-8 hours or till constant weight

Sources & evidence

ORD record
ord-1da639828fe440f0abe51e3580a024b0
Source dataset
uspto-grants-2011_01
Patent number
US07875730B2

Reaction notes

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