Hydrochloric Acid → HCID 90050546, compound

HRID 931379Notes

Reaction equation

HRID 931379 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:14][C:13]1[CH:15]=[C:16]([C:19]([O:21]C)=[O:20])[CH:17]=[CH:18][C:12]=1[O:11]2.[OH-].[Na+].Cl>CO>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:14][C:13]1[CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=[CH:18][C:12]=1[O:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90050547HCID 90050547, compound

Product 1

HCID 90050546HCID 90050546, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2′-oxo-1′,2′-dihydro-3H-spiro[benzofuran-2,3′-pyrrolo[2,3-b]pyridine]-5-carboxylate (100 mg, 0.34 mmol) and aqueous 6 N sodium hydroxide solution (0.17 mL, 1.0 mmol) in MeOH (5 mL) is heated at reflux for 1 h. The mixture is allowed to cool to ambient temperature before it is acidified to pH ˜6 with aqueous 1 N hydrochloric acid solution. The resulting mixture is filtered, and the filtrate is concentrated. The residue is partitioned between water (10 mL) and 2-methyltetrahydrofuran (2-MeTHF, 10 mL). The aqueous layer is extracted with 2-MeTHF (5×10 mL), and the combined organic layers are dried over sodium sulfate and concentrated to provide the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 h
  3. filtrationThe resulting mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. customThe residue is partitioned between water (10 mL) and 2-methyltetrahydrofuran (2-MeTHF, 10 mL)
  6. extractionThe aqueous layer is extracted with 2-MeTHF (5×10 mL)
  7. dry with materialthe combined organic layers are dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-543377cc139442cebdcfcd190546cb59
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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