Ammonia → HCID 21909291, compound

HRID 1826643Notes

Reaction equation

HRID 1826643 reaction equation
[CH2:1]([C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][C:9]=2[OH:18])=[CH:5][CH:4]=1)[CH3:2].[NH3:21].[Cl-].[NH4+]>C(O)C>[CH2:1]([C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([NH2:21])=[O:13])=[CH:10][C:9]=2[OH:18])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 21909266HCID 21909266, compound

Product 1

HCID 21909291HCID 21909291, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of methyl 4-(4-ethylbenzyl)-3-hydroxybenzoate (0.20 g) and 28% aqueous ammonia solution (6 mL) in ethanol (3 mL) was added ammonium chloride (0.079 g), and the mixture was stirred in sealed tube at 100° C. for 14 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. A mixed solvent of dichloromethane and methanol (10:1) was added to the residue, and an insoluble material was collected by filtration and dried to give 4-(4-ethylbenzyl)-3-hydroxybenzamide (0.065 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. additionA mixed solvent of dichloromethane and methanol (10:1) was added to the residue
  7. filtrationan insoluble material was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-a2f8c7fab95148e99e77e6838077eb47
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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