Hydrochloric Acid → HCID 22573180, compound

HRID 1859493Notes

Reaction equation

HRID 1859493 reaction equation
Cl.N[C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[C:8]([O:15][CH3:16])[CH:7]=2.C[O-].[Na+].B.Cl.[OH-].[Na+]>N1C=CC=CC=1.CO>[NH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([C:4]2[CH:3]=[CH:12][C:11]3[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[CH:10]=3)[N:5]=2)[CH2:7]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 12511560HCID 12511560, compound

Product 1

HCID 22573180HCID 22573180, compoundYield 115%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

To a MeOH (3 mL) solution of 4 Å powdered molecular sieves (0.11 g) under argon is added 3-amino-6,7-dimethoxy-quinoline hydrochloride (0.17 g, 0.68 mmol) and NaOMe (0.039 g, 0.71 mmol). The reaction mixture is stirred at room temperature for 30 min., and cyclohexahone (0.074 mL, 0.71 mmol), then pyridine.borane (0.072 mL, 0.071 mmol) are added portionwise. The mixture is stirred for 4.5 h, then 5N HCl (1.4 mL, 6.8 mmol) is added portionwise. The reaction mixture is stirred 45 min., then made strongly basic with 5N NaOH. The mix is partitioned between EtOAC and H2O, and the aqueous layer is washed with EtOAc (2×). The combined organic layers are washed with brine, (1×), dried (MgSO4), chromatographed (50% EtOAc/hexanes), and recrystallized from EtOAc/liexanes to obtain 0.112 g light-yellow solid in 57% yield (m.p. 164-165). Anal. calcd for C17H22N2O2: C, 71.30; H, 7.74; N, 9.78. Found: C, 71.45; H, 7.49; N, 9.80.

Workup

  1. stirringThe mixture is stirred for 4.5 h
  2. stirringThe reaction mixture is stirred 45 min.
  3. customThe mix is partitioned between EtOAC and H2O
  4. washthe aqueous layer is washed with EtOAc (2×)
  5. washThe combined organic layers are washed with brine, (1×),
  6. dry with materialdried (MgSO4)
  7. customchromatographed (50% EtOAc/hexanes)
  8. customrecrystallized from EtOAc/

Sources & evidence

ORD record
ord-7cce76b5c6ca4ee985b173cb0a4d5ddf
Source dataset
uspto-grants-2003_03
Patent number
US06528526B1

Reaction notes

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