Sodium Hydroxide → 4-amino-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one

HRID 1948127Notes

Reaction equation

HRID 1948127 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[C:12]2[C:13](=[O:17])[N:14]([CH3:16])[CH2:15][C:11]=2[CH:10]=[CH:9][N:8]=1.[OH-].[Na+]>Cl>[NH2:6][C:7]1[C:12]2[C:13](=[O:17])[N:14]([CH3:16])[CH2:15][C:11]=2[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 672542684-[(2,4-dimethoxybenzyl)amino]-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one

Product 1

HCID 672535394-amino-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-[(2,4-dimethoxybenzyl)amino]-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one one (1.8 g, 5.7 mmol) in 37% HCl (7.0 mL) was stirred at rt for 16 hours. The reaction mixture was neutralized with NaOH and extracted with EtOAc (15 mL). The organic layer was washed with water (10 mL), washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to yield a red solid. The crude material was purified by silica gel chromatography on the combi-flash Rf system using DCM/MeOH (100:0→95:5) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield an orange solid, (319 mg, 34%). 1H NMR (DMSO-d6, 400 MHz): δ=2.99 (s, 3H), 4.37 (s, 2H), 6.54 (br. s., 2H), 6.73 (d, J=5.05 Hz, 1H), 8.04 (d, J=5.05 Hz, 1H). MS (ES+): m/z 164.07 [MH+] (TOF, polar).

Workup

  1. extractionextracted with EtOAc (15 mL)
  2. washThe organic layer was washed with water (10 mL)
  3. washwashed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a red solid
  8. customThe crude material was purified by silica gel chromatography on the combi-flash Rf system
  9. additionThe fractions containing product
  10. concentrationconcentrated under reduced pressure
  11. customto yield an orange solid, (319 mg, 34%)

Sources & evidence

ORD record
ord-de112d8523fc45e8a6fdc1e6a36c76f7
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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