Sodium Hydroxide → (3-Aminophenyl)(2-methoxyphenyl)methanone

HRID 2231756Notes

Reaction equation

HRID 2231756 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[C:5]([C:7]1[CH:8]=[C:9]([NH:13]C(C2C=CN3C=2CSC3C2C=NC=CC=2)=O)[CH:10]=[CH:11][CH:12]=1)=[O:6].COC1C=CC=CC=1C(C1C=CC=C([N+]([O-])=O)C=1)=O.[OH-].[Na+]>C(O)C>[NH2:13][C:9]1[CH:8]=[C:7]([C:5](=[O:6])[C:4]2[CH:30]=[CH:31][CH:32]=[CH:33][C:3]=2[O:2][CH3:1])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18334149HCID 18334149, compoundHCID 21285575HCID 21285575, compound

Product 1

HCID 21285587(3-Aminophenyl)(2-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
62 °C

Procedure

The 3'-amino-2-methoxybenzophenone may be prepared as follows: Stannous chloride in the dihydrate form (10.3 g) is added, at a temperature between 62° and 66° C., to a suspension of 2-methoxy-3'-nitrobenzophenone (3.9 g) in a mixture of ethanol (40 cc) and concentrated (11.7N) hydrochloric adid (15.2 cc) which is heated to a temperature in the vicinity of 62° C., in the course of 5 minutes. The solution obtained is heated at a temperature in the vicinity of 80° C. for 4 hours, treated with stannous chloride in the dihydrate form (1 g) and heated at a temperature in the vicinity of 80° C. for a further period of 1 hour and then stirred at a temperature in the vicinity of 20° C. for 16 hours. The solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C. The residue is dissolved in distilled water (40 cc) and the solution obtained is adjusted, while maintaining the temperature in the vicinity of 10° C., to a pH in the region of 13 by adding an aqueous 10N sodium hydroxide solution (50 cc) and then extracted 3 times with methylene chloride (150 cc in total). The organic extracts are combined, washed twice with distilled water (200 cc in total), dried over anhydrous magnesium sulphate, treated with decolourizing charcoal (0.5 g), filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa at a temperature in the vicinity of 40° C. 3'- Amino-2-methoxybenzophenone (3.4 g) in the form of greenish yellow crystals, m.p. 81° C., is thereby obtained.

Workup

  1. concentrationconcentrated (11.7N) hydrochloric adid (15.2 cc) which
  2. customThe solution obtained
  3. temperatureis heated at a temperature in the vicinity of 80° C. for 4 hours
  4. temperatureheated at a temperature in the vicinity of 80° C. for a further period of 1 hour
  5. customThe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C
  6. dissolutionThe residue is dissolved in distilled water (40 cc)
  7. customthe solution obtained
  8. temperaturewhile maintaining the temperature in the vicinity of 10° C.
  9. extractionextracted 3 times with methylene chloride (150 cc in total)
  10. washwashed twice with distilled water (200 cc in total)
  11. dry with materialdried over anhydrous magnesium sulphate
  12. additiontreated with decolourizing charcoal (0.5 g)
  13. filtrationfiltered
  14. concentrationconcentrated to dryness under reduced pressure (20 mm Hg
  15. customin the vicinity of 40° C

Sources & evidence

ORD record
ord-df5b6fc8baac41658bc5ac208fb8d627
Source dataset
uspto-grants-1988_11
Patent number
US04783472

Reaction notes

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