5-Aminosalicylic Acid → [2-Hydroxy-5-(2-phenyl-4,5-dihydro-benzo[e]indol-3-yl)-phenyl]-methanediol

HRID 574134Notes

Reaction equation

HRID 574134 reaction equation
O=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]1=O.[NH2:21][C:22]1[CH:30]=[C:26]([C:27]([OH:29])=[O:28])[C:25]([OH:31])=[CH:24][CH:23]=1>C(O)(=O)C>[OH:31][C:25]1[CH:24]=[CH:23][C:22]([N:21]2[C:5]3[CH2:6][CH2:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[C:4]=3[CH:3]=[C:2]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:30][C:26]=1[CH:27]([OH:29])[OH:28]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 122703441-(2-Oxo-2-phenyl-ethyl)-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 68468195[2-Hydroxy-5-(2-phenyl-4,5-dihydro-benzo[e]indol-3-yl)-phenyl]-methanediolYield 50.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3 (2.41 g, 9.1 mmol), 5-aminosalicylic acid (1.40 g, 9.1 mmol) and glacial acetic acid (9 mL) was heated under reflux for 2 hours. After cooling, the precipitate was filtered and washed with acetic acid and water. The solid was recrystallized from acetic acid to afford 1.75 g (50% yield) title product as a yellow solid; MS m/z 380 (M−−H) 9.92 min; 1H NMR (DMSO-d6) δ 2.63 (t, 2H), 2.94 (t, 2H), 4.89 (s, 1H), 7.16 (m, 13H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered
  5. washwashed with acetic acid and water
  6. customThe solid was recrystallized from acetic acid

Sources & evidence

ORD record
ord-5ed5811b5c064c2ca64ef5cb5ad52f74
Source dataset
uspto-grants-2015_05
Patent number
US09034871B2

Reaction notes

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