5-Aminosalicylic Acid → Fendosal

HRID 1659208Notes

Reaction equation

HRID 1659208 reaction equation
[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[Br-].O=[C:14]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:15][CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][C:17]1=[N+]1CCCC1>CO.C(#N)C>[C:7]([C:6]1[CH:10]=[C:2]([N:1]2[C:17]3[CH2:18][CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[C:16]=3[CH:15]=[C:14]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:3]=[CH:4][C:5]=1[OH:11])([OH:9])=[O:8]

Participants

5

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 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.92 g of 5-aminosalicylic acid and 5.0 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), in 75 ml of methanol is refluxed under nitrogen for 9 hours. The solution is allowed to reach ambient temperature before being filtered. The methanol is removed under a vacuum to give a viscous oil which is dissolved in acetonitrile. This solution immediately crystallizes to give a yellow crystalline solid which is collected by filtration and washed with acetonitrile to give 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz[e]indole.

Workup

  1. customto reach ambient temperature
  2. filtrationbefore being filtered
  3. customThe methanol is removed under a vacuum
  4. customto give a viscous oil which
  5. customThis solution immediately crystallizes
  6. customto give a yellow crystalline solid which
  7. filtrationis collected by filtration
  8. washwashed with acetonitrile

Sources & evidence

ORD record
ord-eec206f0166742d2a05667fd027543ef
Source dataset
uspto-grants-1981_12
Patent number
USRE030809

Reaction notes

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