2-Mercaptobenzoic Acid → 2-{[2-(carboxymethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl]sulfanyl}benzoic acid

HRID 126685Notes

Reaction equation

HRID 126685 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[N:7]([CH2:16][C:17]([OH:19])=[O:18])[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.[SH:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:15]=[C:8]1[C:9]2[C:14]3[C:13](=[C:2]([S:21][C:22]4[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=4[C:24]([OH:26])=[O:25])[CH:3]=[CH:4][C:5]=3[C:6](=[O:20])[N:7]1[CH2:16][C:17]([OH:19])=[O:18])[CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 54432-Mercaptobenzoic AcidHCID 11430Potassium CarbonateHCID 150089276-chloro-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid

Product 1

HCID 202878172-{[2-(carboxymethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl]sulfanyl}benzoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid (10.0 g, 34.5 mmoles, described in Example 2); 2-mercaptobenzoic acid (5.85 g, 37.9 mmoles) and anhydrous potassium carbonate (9.54 g, 37.9 mmoles) in dimethylformamide (300 ml) was heated at reflux for 3 hr. The product in the form of its sodium salt was precipitated from the reaction mixture. The precipitate was collected by filtration and dissolved in water. The solution of the sodium salt was rendered acidic with 2 N hydrochloric acid. The resulting precipitate was collected, dried and crystallized from dimethylformamide and water to give 9.0 g of the title compound; mp 339°-341° C.; UV (MeOH) 231, 254, 336 and 346, ε=31,450, 15,810, 8,760 and 9,210, respectively; IR (CHCl3) 2900, 1725, 1710, 1675 cm-1 ; NMR (CDCl3) δ 4.7 (s, 2H), 6.5-8.6 (m, 9H), 13.0 (broad, 1H); Anal. Calc'd: C, 61.91%; H, 3.22%; N, 3.44%; Found: C, 61.51%; H, 3.21%; N, 3.73%.

Workup

  1. temperatureat reflux for 3 hr
  2. customThe product in the form of its sodium salt was precipitated from the reaction mixture
  3. filtrationThe precipitate was collected by filtration
  4. dissolutiondissolved in water
  5. customThe resulting precipitate was collected
  6. customdried
  7. customcrystallized from dimethylformamide and water

Sources & evidence

ORD record
ord-046073ca8f994b239b524159e77e8f76
Source dataset
uspto-grants-1981_03
Patent number
US04254109

Reaction notes

Loading…