Hydrochloric Acid → (3-Aminophenyl)(3-methylphenyl)methanone

HRID 2231745Notes

Reaction equation

HRID 2231745 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[C:5]([C:7]1[CH:8]=[C:9]([NH:13]C(CC2C=CN3C=2CSC3C2C=NC=CC=2)=O)[CH:10]=[CH:11][CH:12]=1)=[O:6].CC1C=C(C(=O)C2C=CC=C([N+]([O-])=O)C=2)C=CC=1.Cl>C(O)C>[NH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:5]([C:4]1[CH:31]=[CH:32][CH:33]=[C:2]([CH3:1])[CH:3]=1)=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21285581HCID 21285581, compoundHCID 131715768HCID 131715768, compound

Product 1

HCID 21285570(3-Aminophenyl)(3-methylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

The 3-amino-3'-methylbenzophenone may be prepared as follows: stannous chloride in the dihydrate form(19 g) is added, at a temperature between 40° and 80° C., to a suspension of 3'-methyl-3-nitrobenzophenone (6.8 g) in a mixture of ethanol (80 cc) and concentrated hydrochloric acid (30 cc), in the course of 10 minutes. The solution obtained is heated at a temperature in the vicinity of 85° C. for 3 hours 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 60° C. The residue is suspended in distilled water (300 cc). An aqueous 10N sodium hydroxide solution (100 cc) is added, at a temperature in the vicinity of 20° C., with stirring, to the suspension obtained and extraction is carried out 3 times with diethyl ether (550 cc in total). The ether extracts are combined, washed twice with distilled water (300 cc in total) and then 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 50° C. 3-Amino-3'-methylbenzophenone (5.7 g) in the form of yellow crystals, m.p. 110° C., is thereby obtained.

Workup

  1. customThe solution obtained
  2. customThe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C
  3. additionAn aqueous 10N sodium hydroxide solution (100 cc) is added, at a temperature in the vicinity of 20° C.
  4. stirringwith stirring, to the suspension
  5. customobtained
  6. extractionextraction
  7. washwashed twice with distilled water (300 cc in total)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. additiontreated with decolourizing charcoal (0.5 g)
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C

Sources & evidence

ORD record
ord-b223f025862e4e92bd84628e86e5447c
Source dataset
uspto-grants-1988_11
Patent number
US04783472

Reaction notes

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