Ethanol → Tacedinaline

HRID 1776959Notes

Reaction equation

HRID 1776959 reaction equation
FC(F)(F)C(O)=O.[C:8]([NH:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])=[O:17])=[CH:14][CH:13]=1)(=[O:10])[CH3:9].CCO.C([O-])(O)=O.[Na+]>O>[C:8]([NH:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])=[O:17])=[CH:14][CH:13]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 56596977HCID 56596977, compound

Product 1

HCID 2746TacedinalineYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dried solid of 4-acetamido-N-(2-aminophenyl)benzamide trifluoroacetate salt was suspended in a solution of 1:1 EtOH:H2O (320 mL). Saturated NaHCO3 solution (100 mL) was added slowly to adjust the pH to 8. The resultant slurry was stirred for 1.5 hours. The precipitates were filtered and washed with water (2×60 mL). After drying at 40° C. in vacuo for 16 h, 4-acetamido-N-(2-aminophenyl)benzamide (21.3 g, 92% yield, 97.0% HPLC purity) was isolated as crystalline Form B (white solid).

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water (2×60 mL)
  3. customAfter drying at 40° C. in vacuo for 16 h

Sources & evidence

ORD record
ord-08227774236f46ae902c12351c3582aa
Source dataset
uspto-grants-2016_02
Patent number
US09266822B2

Reaction notes

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