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

HRID 511555
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HRID 511555 반응식
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
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

A solution of 4-[(2,4-dimethoxybenzyl)amino]-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-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, 3 H), 4.37 (s, 2 H), 6.54 (br. s., 2 H), 6.73 (d, J=5.05 Hz, 1 H), 8.04 (d, J=5.05 Hz, 1 H). MS (ES+): m/z 164.07 [MH+] (TOF, polar).

후처리

  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%)

출처 및 근거

ORD 기록
ord-01b5a5ca82384357b3615d42b867fa01
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096624B2

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