Hydrochloric Acid → HCID 6914595, compound

HRID 892284Notes

Reaction equation

HRID 892284 reaction equation
[OH:1][C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[C:4]([CH:13]=[CH:14][C:15]=1[O:16]C)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[Cl-].[Al+3].[Cl-].[Cl-].N1C=CC=CC=1.Cl>ClCCCl>[OH:1][C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[C:4]([CH:13]=[CH:14][C:15]=1[OH:16])[C:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6451240Aluminum(III) ChlorideHCID 22242329(3-Hydroxy-4-methoxy-2-nitrophenyl)(phenyl)methanone

Product 1

HCID 6914595HCID 6914595, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of 3-Hydroxy4-methoxy-2-nitrobenzophenone (8.3 g, 30.38 mmol) in 1,2-dichloroethane (100 ml) at room temperature under argon was added aluminium chloride (4.46 g, 33.45 mmol) in one portion followed by pyridine (9.61 g, 9.81 ml, 121.5 mmol) giving rise to an exothermic reaction. the mixture was stirred at reflux for one hour, allowed to cool to room temperature and then poured onto ice-water (300 ml). Hydrochloric acid (2N, 70 ml) was added and the mixture was stirred for one hour (initial orange precipitate gradually became yellow in appearance. The solid was removed by filtration, washed by water (30 ml) and dried under vacuum to give the product as a yellow solid 6.99 g, (89%) of melting point 153–155° C. The organic phase of the filtrate was separated and the aqueous phase was extracted by dichloromethane (20 ml). The combined organic phases were washed by brine (30 ml), dried over anhydrous sodium sulphate and the solvent removed on a rotary evaporator (bath temp. 40° C.) to leave a yellow solid (0.7 g) which was not purified further.

Workup

  1. customgiving rise
  2. customto an exothermic reaction
  3. temperatureat reflux for one hour
  4. additionpoured onto ice-water (300 ml)
  5. stirringthe mixture was stirred for one hour (initial orange precipitate gradually became yellow in appearance
  6. customThe solid was removed by filtration
  7. washwashed by water (30 ml)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-62634ca5dd0643a4ada33ab0e73a0ce5
Source dataset
uspto-grants-2006_02
Patent number
US07005553B2

Reaction notes

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