Benzophenone → HCID 178435844, compound

HRID 255862Notes

Reaction equation

HRID 255862 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][C:8](C(O)=O)=[C:7]2[OH:15].[C:16](C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCOCC>[CH2:1]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][CH:8]=[C:7]2[OH:15])[CH3:16]

Participants

4

Reactant 2

HCID 3102BenzophenoneHCID 178423905HCID 178423905, compound

Product 1

HCID 178435844HCID 178435844, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 0.7 g of 53D and 2.8 g of benzophenone was heated at 180°-210° C. until no more gas evolved (30 minutes). The mixture was cooled to 0° C., diluted with ether and filtered. The solid was slurried with hot 5 N aqueous sodium hydroxide solution and filtered. The filtrate was acidified with 12 N hydrochloric acid, allowed to cool and stand overnight at room temperature, and filtered. The resulting solid was dried under reduced pressure, and flash chromatographed on silica gel, using a 1:1 v:v mixture of ethyl acetate and methylene chloride as eluent, to give 8-ethyl-4-hydroxycinnoline (53E), as a solid, m.p.: 160°-161° C.

Workup

  1. temperaturewas heated at 180°-210° C. until no more gas
  2. custom(30 minutes)
  3. filtrationfiltered
  4. filtrationfiltered
  5. temperatureto cool
  6. filtrationfiltered
  7. customThe resulting solid was dried under reduced pressure, and flash
  8. customchromatographed on silica gel
  9. additionv mixture of ethyl acetate and methylene chloride as eluent

Sources & evidence

ORD record
ord-bcc1aaf0ee004f34b1beb997bc967ea9
Source dataset
uspto-grants-1987_10
Patent number
US04699651

Reaction notes

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