HCID 12639764, compound → HCID 12639769, compound

HRID 1731162Notes

Reaction equation

HRID 1731162 reaction equation
[CH3:1][C:2]1[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5]>Cl>[CH3:1][C:2]1[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=[O:5]

Participants

3

Reactant 1

HCID 12639764HCID 12639764, compound

Product 1

HCID 12639769HCID 12639769, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
62 °C

Procedure

A mixture of 3,750 ml of hydrochloric acid, 134 g of 2-methyl-3-nitro-4'-chloro-benzophenone and 536 g of stannous chloride was heated at 62° C for 6 hours and was then cooled to 5° C and held therefor 1 hour. The mixture was vacuum filtered and the precipitate was washed with hydrochloric acid and dried under reduced pressure. The residue was stirred for 2 hours at room temperature with 1,300 ml of water, 1,000 ml of 2N sodium hydroxide and 230 ml of ether and the mixture was then extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulfate and evaporated to dryness under reduced pressure to obtain 68.7 g of 2-methyl-3-amino-4'-chloro-benzophenone melting at 65° C which was used as is for the next step.

Workup

  1. temperaturewas then cooled to 5° C
  2. custom1 hour
  3. filtrationfiltered
  4. washthe precipitate was washed with hydrochloric acid
  5. customdried under reduced pressure
  6. extractionthe mixture was then extracted with methylene chloride
  7. washThe organic phase was washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-98a3fb217b9d4e9a9245a36e46c5562a
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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