Hydrochloric Acid → HCID 21285560, compound

HRID 2231752Notes

Reaction equation

HRID 2231752 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1[CH:33]=[CH:32][C:6]([C:7]([C:9]2[CH:10]=[C:11]([NH:15]C(C3C=CN4C=3CSC4C3C=NC=CC=3)=O)[CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:4]=1.CN(C)C1C=CC(C(=O)C2C=CC=C([N+]([O-])=O)C=2)=CC=1.Cl.[OH-].[Na+]>O.C(O)(C)C.C(O)C>[NH2:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[C:7]([C:6]1[CH:32]=[CH:33][C:3]([N:2]([CH3:34])[CH3:1])=[CH:4][CH:5]=1)=[O:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13378616[4-(Dimethylamino)phenyl](3-nitrophenyl)methanoneHCID 21285561HCID 21285561, compound

Product 1

HCID 21285560HCID 21285560, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
79 °C

Procedure

The 3-amino-4'-dimethylaminobenzophenone may be prepared as follows: Stannous chloride in the dihydrate form (29.3 g) is added, at a temperature between 44° and 79° C., to a suspension of 4'-dimethylamino-3-nitrobenzophenone (11.4 g) in a mixture of concentrated hydrochloric acid (45 cc) and ethanol (120 cc), in the course of 35 minutes. The solution obtained is heated at a temperature in the vicinity of 79° C. for 3 hours. The suspension obtained is concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C. The residue obtained is suspended in distilled water (350 cc) and an aqueous 10N sodium hydroxide solution (100 cc) is added, at a temperature in the vicinity of 5° C., to the suspension obtained and the mixture is stirred at a temperature in the vicinity of 20° C. for 30 minutes. The crystals formed are separated by filtration, washed 3 times with distilled water (60 cc in total) and air-dried. The crude product obtained is dissolved in boiling isopropanol (30 cc) and the solution obtained is cooled at a temperature in the vicinity of 4° C. for 2 hours. The crystals formed are separated by filtration, washed twice with isopropanol cooled to a temperature in the vicinity of 4° C. (20 cc in total) and twice with diethyl ether (40 cc) and then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets. 3-amino-4'-dimethylaminobenzophenone (8.4 g) in the form of beige-coloured crystals, m.p. 110° C., is thereby obtained.

Workup

  1. customThe solution obtained
  2. customThe suspension obtained
  3. concentrationis concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C
  4. customThe residue obtained
  5. customobtained
  6. customThe crystals formed
  7. customare separated by filtration
  8. washwashed 3 times with distilled water (60 cc in total)
  9. customair-dried
  10. customThe crude product obtained
  11. dissolutionis dissolved
  12. customthe solution obtained
  13. temperatureis cooled at a temperature in the vicinity of 4° C. for 2 hours
  14. customThe crystals formed
  15. customare separated by filtration
  16. washwashed twice with isopropanol
  17. temperaturecooled to a temperature in the vicinity of 4° C. (20 cc in total) and twice with diethyl ether (40 cc)
  18. dry with materialdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-49019220c48f4f188321ba58fd8af03d
Source dataset
uspto-grants-1988_11
Patent number
US04783472

Reaction notes

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