5-Aminosalicylic Acid → HCID 12270313, compound

HRID 1579906Notes

Reaction equation

HRID 1579906 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)[C:7](=O)[CH2:6][CH2:5]2.[NH2:22][C:23]1[CH:31]=[C:27]([C:28]([OH:30])=[O:29])[C:26]([OH:32])=[CH:25][CH:24]=1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>>[C:28]([C:27]1[CH:31]=[C:23]([N:22]2[C:7]3[CH2:6][CH2:5][C:4]4[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]=4[C:8]=3[CH:12]=[C:13]2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:24]=[CH:25][C:26]=1[OH:32])([OH:30])=[O:29]

Participants

4

Reactant 3

HCID 40755-Aminosalicylic AcidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 122703422(1H)-Naphthalenone, 6-chloro-3,4-dihydro-1-(2-oxo-2-phenylethyl)-

Product 1

HCID 12270313HCID 12270313, compound

Procedure

A mixture of 10.1 g. (0.03 mole) of 6-chloro-1-phenacyl-2-tetralone, 4.5 g. (0.03 mole) of 5-aminosalicylic acid and 30 ml. of glacial acetic was heated under reflux for 70 minutes, cooled and filtered. The collected solid was washed with acetic acid and petroleum ether and recrystallized from acetonitrile to give 4.3 g. (59%) of colorless crystals, m.p. 249°-251°.

Workup

  1. additionA mixture of 10.1 g
  2. temperatureunder reflux for 70 minutes
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe collected solid was washed with acetic acid and petroleum ether
  6. customrecrystallized from acetonitrile
  7. customto give 4.3 g

Sources & evidence

ORD record
ord-520cfdc009d849d29f7d7af0ad47a115
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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