5-Aminosalicylic Acid → Fendosal

HRID 1833394Notes

Reaction equation

HRID 1833394 reaction equation
Br.[CH2:2]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]=1N(C)C)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:24][C:25]1[CH:33]=[C:29]([C:30]([OH:32])=[O:31])[C:28]([OH:34])=[CH:27][CH:26]=1>C(O)(=O)C>[C:30]([C:29]1[CH:33]=[C:25]([N:24]2[C:12]3[CH2:13][CH2:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]=3[CH:2]=[C:3]2[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:26]=[CH:27][C:28]=1[OH:34])([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 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 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-3c89a94c5e9c44b9b483d1d7a38fa104
Source dataset
uspto-grants-1978_01
Patent number
US04066659

Reaction notes

Loading…