5-Aminosalicylic Acid → HCID 12270303, compound

HRID 1579890Notes

Reaction equation

HRID 1579890 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[C:3](=O)[CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=O.[NH2:19][C:20]1[CH:28]=[C:24]([C:25]([OH:27])=[O:26])[C:23]([OH:29])=[CH:22][CH:21]=1>C(O)(=O)C>[C:2]([C:3]1[N:19]([C:20]2[CH:21]=[CH:22][C:23]([OH:29])=[C:24]([C:25]([OH:27])=[O:26])[CH:28]=2)[C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[CH:4]=1)([CH3:18])([CH3:17])[CH3:1]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 12270338HCID 12270338, compound

Product 1

HCID 12270303HCID 12270303, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 15.2 g. (0.062 mole) of 1-(3,3-dimethyl-2-oxobutyl)-2-tetralone, 9.5 g. (0.062 mole) of 5-aminosalicylic acid, and 50 ml. of glacial acetic acid was heated under reflux under nitrogen for 1.5 hours, cooled and filtered. The collected solid was washed with acetic acid and petroleum ether and then recrystallized from acetonitrile to provide 10.4 g. (46%) of off-white crystals, m.p. 258°-260°.

Workup

  1. additionA mixture of 15.2 g
  2. temperatureunder reflux under nitrogen for 1.5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe collected solid was washed with acetic acid and petroleum ether
  6. customrecrystallized from acetonitrile
  7. customto provide 10.4 g

Sources & evidence

ORD record
ord-23ee49cd75794080a6a21deb17ae3e4a
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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