1-Bromopropane → HCID 21250793, compound

HRID 437427Notes

Reaction equation

HRID 437427 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([NH2:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1.[Na].Br[CH2:15][CH2:16][CH3:17]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:12][CH2:15][CH2:16][CH3:17])=[C:7]([CH:11]=1)[C:8]([NH2:10])=[O:9]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 119977Salicylamide, 5-methoxy-HCID 5360545Sodium

Product 1

HCID 21250793HCID 21250793, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Methoxysalicylamide (56.0 g., 0.335 mole) was added to a cooled, stirred solution of sodium (8.55 g., 0.372 g-atom) in ethanol (335 ml.). To the resulting suspension was added 1-bromopropane (41.3 g., 0.335 mole) dropwise over 20 minutes. The mixture was stirred at room temperature for one hour, then was heated under reflux for 19 hours. The solvent was removed under reduced pressure. The residue was treated with cold water (500 ml.). The solid was collected by filtration and recrystallized from acetonitrile to give 5-methoxy-2-n-propoxybenzamide (29.0 g., 41.4%), m.p. 83°-87°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. customThe solvent was removed under reduced pressure
  4. additionThe residue was treated with cold water (500 ml.)
  5. filtrationThe solid was collected by filtration
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-c8e32278ceaf470584069d0c3dfe8b59
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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