Sodium Hydroxide → HCID 22822243, compound

HRID 1902551Notes

Reaction equation

HRID 1902551 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[C:14]([N:17]=[C:18]1[N:22]3[CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[CH2:30][C@H:21]3[CH2:20][S:19]1)[CH:13]=[CH:12][CH:11]=2)=[O:5])C.[OH-].[Na+]>Cl>[C:4]([CH2:6][C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[C:14]([N:17]=[C:18]1[N:22]3[CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[CH2:30][C@H:21]3[CH2:20][S:19]1)[CH:13]=[CH:12][CH:11]=2)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22822254HCID 22822254, compound

Product 1

HCID 22822243HCID 22822243, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

A solution of (S)-3-[(3-ethoxycarbonylmethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline (3.8 g) in 3 N hydrochloric acid (60 cc) is heated at 100° C. for 6 hours. After cooling, the pH of the solution is adjusted to 7 by adding 5 N sodium hydroxide solution, and the mixture is then extracted with methylene chloride (2×200 cc). The organic extracts are combined, dried over magnesium sulphate and then concentrated to dryness. The resulting residue is dissolved in a dimethylformamide/water mixture (2/1 by volume; 60 cc), the solution is heated to the boil, decolorising charcoal (0.3 g) is added and the mixture is filtered hot. After cooling at 5° C. for 20 hours, the crystals which have appeared are filtered off, washed with diisopropyl ether and then dried at 70° C. under reduced pressure (0.1 mm Hg; 0.013 kPa) to yield (S)-3-[(3-carboxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (1.7 g), melting at about 200° C. (with decomposition).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is then extracted with methylene chloride (2×200 cc)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness
  5. dissolutionThe resulting residue is dissolved in a dimethylformamide/water mixture (2/1 by volume; 60 cc)
  6. temperaturethe solution is heated to the boil
  7. additionis added
  8. filtrationthe mixture is filtered hot
  9. filtrationthe crystals which have appeared are filtered off
  10. washwashed with diisopropyl ether
  11. customdried at 70° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-846c11de7b214a25918de7d0a86883eb
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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