Sodium Hydroxide → HCID 67316387, compound

HRID 1013881Notes

Reaction equation

HRID 1013881 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, 1H), 7.25 (d, 1H), 7.16 (d, 1H), 4.87 (br, 1H), 1.73 (d, 6H).

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-e45ac402259d4ee290c0ff4b163c0983
Source dataset
uspto-grants-2011_07
Patent number
US07982040B2

Reaction notes

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