5-Aminosalicylic Acid → Fendosal

HRID 1659209Notes

Reaction equation

HRID 1659209 reaction equation
[Br-].O=[C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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+](C)C.Br.C(C1C2C(=CC=CC=2)CCC=1N(C)C)C(C1C=CC=CC=1)=O.[NH2:47][C:48]1[CH:56]=[C:52]([C:53]([OH:55])=[O:54])[C:51]([OH:57])=[CH:50][CH:49]=1>C(O)(=O)C>[C:53]([C:52]1[CH:56]=[C:48]([N:47]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:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:49]=[CH:50][C:51]=1[OH:57])([OH:55])=[O:54]

Participants

5

Reactant 3

HCID 40755-Aminosalicylic AcidHCID 20559866HCID 20559866, compoundHCID 20559874HCID 20559874, compound

Product 1

HCID 40821Fendosal

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 10.0 g of tautomeric N-[3,4-dihydro-1-(2-oxo-2-phenylethyl)-2(1H)-naphthalenylidene]-N-methylmethanaminium bromide in equilibrium with 1-phenacyl-2-dimethylamino-3,4-dihydronaphthalene hydrobromide and 4.1 g of 5-aminosalicylic acid in 50 ml of acetic acid is vigorously stirred at 75° C. for 4.5 hours. The reaction mixture is then cooled to 20° C., filtered and the precipitate collected, washed successively with one 20 ml portion of acetic acid and five 20 ml portions of hexane and then dried for 20 hours under vacuum to give 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz[e]indole.

Workup

  1. temperatureThe reaction mixture is then cooled to 20° C.
  2. filtrationfiltered
  3. customthe precipitate collected
  4. washwashed successively with one 20 ml portion of acetic acid and five 20 ml portions of hexane
  5. customdried for 20 hours under vacuum

Sources & evidence

ORD record
ord-8822c70ec2b840af8475421a12c14fb7
Source dataset
uspto-grants-1981_12
Patent number
USRE030809

Reaction notes

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