Salicylic Acid → HCID 178489624, compound

HRID 254871Notes

Reaction equation

HRID 254871 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:40])(=[O:39])[C:32]1[C:33](=[CH:35][CH:36]=[CH:37][CH:38]=1)[OH:34]>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-:40])(=[O:39])[C:32]1[C:33](=[CH:35][CH:36]=[CH:37][CH:38]=1)[OH:34]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 17130052-(2-Methoxyphenoxy)ethyl amineHCID 50207104-Oxiranylmethoxy-9H-carbazole

Product 1

HCID 178489624HCID 178489624, compoundYield 70%

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 the reaction mass is then raised to 80° C. to 82° C. and refluxed for 1 hour. The reaction mixture is added into the preheated (80° C. to 85° C.) solution of salicylic acid (18.77 g, 135.98 mmoles) in 187.5 ml of 2-propanol. The reaction mass is further refluxed for 2 hours, cooled to 50° C. to 55° C. and stirred for 1 hour at this temperature. The solid is filtered, followed by three 33 ml wash with hot (50° C. to 55° C.) 2-propanol. The wet product dried at 60° C. to 65° C. for 6 hours or till constant weight gives 39.75 g (Yield 70%) of Carvedilol salicylate, which contains about 2-2.5% of compound (IV) as an impurity.

Workup

  1. temperatureis heated to 70° C. to 80° C
  2. temperatureThe temperature of the reaction mass is then raised to 80° C. to 82° C.
  3. temperaturerefluxed for 1 hour
  4. temperatureThe reaction mass is further refluxed for 2 hours
  5. temperaturecooled to 50° C. to 55° C.
  6. filtrationThe solid is filtered
  7. washwash with hot (50° C. to 55° C.) 2-propanol
  8. customThe wet product dried at 60° C. to 65° C. for 6 hours or till constant weight

Sources & evidence

ORD record
ord-6f2a920473da4cfb80645e85af44900e
Source dataset
uspto-grants-2011_01
Patent number
US07875730B2

Reaction notes

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