Sodium Hydroxide → HCID 20287803, compound

HRID 126691Notes

Reaction equation

HRID 126691 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][N:6]1[C:15](=[S:16])[C:14]2[CH:17]=[CH:18][CH:19]=[C:12]3[C:13]=2[C:8](=[CH:9][CH:10]=[CH:11]3)[C:7]1=[O:20])C.[OH-].[Na+]>CO>[O:20]=[C:7]1[C:8]2[C:13]3[C:12](=[CH:19][CH:18]=[CH:17][C:14]=3[C:15](=[S:16])[N:6]1[CH2:5][C:4]([OH:21])=[O:3])[CH:11]=[CH:10][CH:9]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53752917HCID 53752917, compound

Product 1

HCID 20287803HCID 20287803, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 1-oxo-3-thioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid ethyl ester (34.35 g, 0.115 mole, described in Example 6) in methanol (200 ml) and aqueous 4 N sodium hydroxide (43 ml, 0.1721 mole) was stirred at 20° C. for 18 hr. The solvent was removed and the residue suspended in water (1 liter). The aqueous suspension was extracted with ethyl acetate (2×1 liter) to remove unreacted ethyl ester. The aqueous phase was rendered acidic with 2 N hydrochloric acid. The resulting precipitate was collected. Recrystallization of the precipitate from methanol gave 22.5 g of the title compound, mp 265° C. (dec.); UV (MeOH) 244, 251, 333, 344, 390 nm, ε=20,210, 19,150, 8,640, 8,225, 13,995, respectively; IR (nujol) 2900, 1720 and 1683 cm-1 ; NMR (DMSO-d6) δ5.33 (s, 2H), 7.3-8.93 (m, 6H); Anal. Calc'd.: C, 61.98%; H, 3.34%; N, 5.16%; Found: C, 62.07%; H, 3.42%, N, 5.00%.

Workup

  1. customThe solvent was removed
  2. extractionThe aqueous suspension was extracted with ethyl acetate (2×1 liter)
  3. customto remove unreacted ethyl ester
  4. customThe resulting precipitate was collected
  5. customRecrystallization of the precipitate from methanol

Sources & evidence

ORD record
ord-587b62d842ba4eeba3cfd3d3c60eef4b
Source dataset
uspto-grants-1981_03
Patent number
US04254108

Reaction notes

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