Ammonia → HCID 21909291, compound

HRID 1982841Notes

Reaction equation

HRID 1982841 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 at 100° C. in a sealed tube for 14 hours. The reaction mixture was concentrated, and water was added to the residue. The mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and to the residue was added a mixture (10/1) of dichloromethane and methanol. Insoluble materials were collected and dried to give 4-(4-ethylbenzyl)-3-hydroxybenzamide (0.065 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. extractionThe 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. additionto the residue was added a mixture (10/1) of dichloromethane and methanol
  7. customInsoluble materials were collected
  8. customdried

Sources & evidence

ORD record
ord-73ca7cb60e614fb09a3e2cbfda3d5abf
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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