Phosphoric Acid → 7-Quinolinol, 1,2,3,4-tetrahydro-

HRID 1731609Notes

Reaction equation

HRID 1731609 reaction equation
C1(=O)O[C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][C:13]1C=CC=C[C:14]=1O.P(=O)(O)(O)[OH:21].Cl(O)(=O)(=O)=O>CO>[OH:21][C:9]1[CH:10]=[C:2]2[C:3]([CH2:4][CH2:14][CH2:13][NH:12]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 58012-AminophenolHCID 6811Phthalic AnhydrideHCID 24247Perchloric Acid

Product 1

HCID 939807-Quinolinol, 1,2,3,4-tetrahydro-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

and phthalic anhydride 3.0 g. were heated as described in Example 11. Another 3.0 g. of the amino-phenol and 85% phosphoric acid 8 ml. were added and the contents heated under reflux in an oil-bath at 170° for three hours. A solution of 50% aqueous perchloric acid 8 ml. in methanol 80 ml. was added to the cooled reaction, the mixture refluxed and cooled at 0° overnight. Filtration gave 5.0 g. (44%) of dark red crystals.

Workup

  1. temperaturewere heated
  2. additionwere added
  3. temperaturethe contents heated
  4. temperatureunder reflux in an oil-bath at 170° for three hours
  5. additionwas added to the cooled reaction
  6. temperaturethe mixture refluxed
  7. temperaturecooled at 0° overnight
  8. filtrationFiltration
  9. customgave 5.0 g

Sources & evidence

ORD record
ord-7daeb652a7ed468281ea3764f0f95fad
Source dataset
uspto-grants-1986_11
Patent number
US04622400

Reaction notes

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