Sodium Hydroxide → HCID 67316387, compound

HRID 1724663Notes

Reaction equation

HRID 1724663 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]([O:13]CC)=[O:12])=[CH:7][C:6]2[CH:16]=[CH:17][S:18][C:5]1=2)([CH3:3])[CH3:2].[OH-].[Na+]>CO>[CH:1]([N:4]1[C:9](=[O:10])[C:8]([C:11]([OH:13])=[O:12])=[CH:7][C:6]2[CH:16]=[CH:17][S:18][C:5]1=2)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67317348HCID 67317348, compound

Product 1

HCID 67316387HCID 67316387, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 6,7-dihydro-7-isopropyl-6-oxothieno[2,3-b]pyridine-5-carboxylate (1.12 g, 4.2 mmol), sodium hydroxide (6.3 mL, 2 N solution in water, 12.6 mmol) and methanol (20 mL) was heated at reflux for 18 h, cooled to room temperature and concentrated to remove methanol. The concentrate was diluted with water, cooled to 0° C. and acidified with concentrated hydrochloric acid. The resulting precipitates were collected by vacuum filtration and dried to provide the title compound as an off-white solid (0.81 g, 82% yield). 1H NMR (400 MHz, CDCl3): □ 8.86 (s, 1 H), 7.25 (d, 1 H), 7.16 (d, 1 H), 4.87 (br, 1 H), 1.73 (d, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated
  4. customto remove methanol
  5. additionThe concentrate was diluted with water
  6. temperaturecooled to 0° C.
  7. customThe resulting precipitates
  8. filtrationwere collected by vacuum filtration
  9. customdried

Sources & evidence

ORD record
ord-bbd42a5667cb41c98a0367404bb2c15e
Source dataset
uspto-grants-2009_02
Patent number
US07488736B2

Reaction notes

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