Hydrochloric Acid → HCID 67222672, compound

HRID 633836Notes

Reaction equation

HRID 633836 reaction equation
Cl.C([SiH2][O:7][C:8](C)(C)[CH:9]1[CH2:23][C:12]2=[C:13]3[C:18](=[N:19][CH:20]=[C:11]2[O:10]1)[CH:17]=[CH:16][C:15]([O:21][CH3:22])=[N:14]3)(C)(C)C>CO>[CH3:22][O:21][C:15]1[CH:16]=[CH:17][C:18]2[C:13]([N:14]=1)=[C:12]1[CH2:23][CH:9]([CH2:8][OH:7])[O:10][C:11]1=[CH:20][N:19]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178487801HCID 178487801, compound

Product 1

HCID 67222672HCID 67222672, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2.0 N hydrochloric acid aqueous solution (5 mL) is added at room temperature to a stirred solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalene (600 mg, 1.7 mmol, 1.0 eq) in methanol (20 mL). After 2 hours stirring at room temperature, solvent is removed, the residue is extracted with dichloromethane (3×30 mL) and water (30 mL) and the pH is adjusted to 8 by the addition of a saturated sodium carbonate aqueous solution. The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to afford (8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalene-2-yl)-methanol as an off-white solid (400 mg, 99% yield).

Workup

  1. customsolvent is removed
  2. extractionthe residue is extracted with dichloromethane (3×30 mL) and water (30 mL)
  3. additionthe pH is adjusted to 8 by the addition of a saturated sodium carbonate aqueous solution
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3c773f3839894651a680a9ba9ac0c034
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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