Acetamide → HCID 59620386, compound

HRID 1887719Notes

Reaction equation

HRID 1887719 reaction equation
[O:1]=[C:2]1[CH:11]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(N)(=O)C.C([O-])(=O)C.[Na+].[Br:25]Br>C(O)(=O)C.O>[Br:25][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[CH:11]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10]2

Participants

7

Reactant 4

HCID 178AcetamideHCID 24408BromineHCID 517045Sodium AcetateHCID 44521548HCID 44521548, compound

Product 1

HCID 59620386HCID 59620386, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

Acetic acid (3,240 mL) was added to N-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetamide (405.8 g), and the acetamide was dissolved in acetic acid at an inside temperature of 51° C. The reactor was cooled to an inside temperature of 25° C., and sodium acetate was added thereto. To the mixture maintained at an inside temperature of 25° C., bromine was dropwise added over 30 minutes under stirring. The reaction mixture was added to water (35 L), and the reactor was washed with water (3.24 L). The thus-obtained mixture was stirred at 24° C. for one hour.

Workup

  1. additionwas added
  2. additionwas dropwise added over 30 minutes
  3. washthe reactor was washed with water (3.24 L)
  4. stirringThe thus-obtained mixture was stirred at 24° C. for one hour

Sources & evidence

ORD record
ord-e4ecc955086b4c54be4b9c4487ff64c6
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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