Hydrochloric Acid → HCID 21964341, compound

HRID 270168Notes

Reaction equation

HRID 270168 reaction equation
[OH-].[Na+].CO.C([O:7][C:8]([C:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)=[CH:13][S:12][C:11]=1[N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32])=[O:9])C.Cl>O>[O:31]=[C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:32])[N:22]1[C:11]1[S:12][CH:13]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[C:10]=1[C:8]([OH:9])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67073683HCID 67073683, compound

Product 1

HCID 21964341HCID 21964341, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of NaOH (1.4 mmol) in a 1:1 mixture of methanol:H2O (6 mL) was added 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-4-(3-methylphenyl)-thiophene-3-carboxylic acid ethyl ester (0.7 mmol, Example 2 & 3, Part C). The mixture was heated to reflux for 90 min, then diluted with water (12 mL), chilled in an ice bath, and acidified with concentrated HCl. The product that precipitated was collected by filtration, washed with water, and dried, affording the desired compound as a white solid in 94% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 90 min
  3. temperaturechilled in an ice bath
  4. customThe product that precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b2d88123f3504f9d861d7425f4de7a0e
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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