5-Aminosalicylic Acid → Fendosal

HRID 1659207Notes

Reaction equation

HRID 1659207 reaction equation
[Br-].O=[C:3]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[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=[N+]1CCCC1.[NH2:26][C:27]1[CH:35]=[C:31]([C:32]([OH:34])=[O:33])[C:30]([OH:36])=[CH:29][CH:28]=1>C(O)(=O)C>[C:32]([C:31]1[CH:35]=[C:27]([N:26]2[C:6]3[CH2:7][CH2:8][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:5]=3[CH:4]=[C:3]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:28]=[CH:29][C:30]=1[OH:36])([OH:34])=[O:33]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 205598811-[3,4-dihydro-1-(2-oxo-2-phenylethyl)-2(1H)-naphthalenylidene]pyrrolidinium bromide

Product 1

HCID 40821Fendosal

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A well stirred mixture of 3.98 g of tautomeric 1-[3,4-dihydro-1-(2-oxo-2-phenylethyl)-2(1H)-naphthalenylidene]pyrrolidinium bromide in equilibrium with 1-phenacyl-2-(1-pyrrolidino)-3,4-dihydronaphthalene hydrobromide (Example 1a), 1.53 g of 5-aminosalicylic acid and 10 ml of acetic acid is heated at reflux for 15 minutes. The reaction mixture is allowed to stand at ambient temperature and then diluted with 10 ml of acetic acid. The resulting solid is collected by suction filtration, washed with 50 ml of petroleum ether and then dried under high vacuum for 72 hours to give 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz[e]indole.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 15 minutes
  3. customto stand at ambient temperature
  4. filtrationThe resulting solid is collected by suction filtration
  5. washwashed with 50 ml of petroleum ether
  6. customdried under high vacuum for 72 hours

Sources & evidence

ORD record
ord-f49c0569085f4477ae16c4e8c3b6f7d6
Source dataset
uspto-grants-1981_12
Patent number
USRE030809

Reaction notes

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