Hydrochloric Acid → 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-

HRID 217956ノート

反応式

HRID 217956 の反応式
C([O:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:8]=1)=[O:6])CC.[OH-].[Na+].Cl>C(O)C>[C:19]([N:9]1[C:10]2=[N:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[C:15]2[C:7]([C:5]([OH:6])=[O:4])=[CH:8]1)([CH3:22])([CH3:20])[CH3:21]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669245181H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-, propyl ester

生成物 1

HCID 669243961H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-収率 89.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of 5.00 g (16.38 mmol) of 1-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid propyl ester in 50 mL of 95° ethanol, it was added 2M NaOH (50 mL; 100 mmol) under stirring. The mixture was heated to reflux for 1 hour obtaining the complete consumption of the substrate. The resulting solution was cooled to room temperature and concentrated under reduced pressure to a slurry that was diluted with 250 mL of water and washed with 100 mL of a 1:1 mixture of diethyl ether and ethyl acetate. The aqueous layer was treated with 5M HCl (37 mL; 185 mmol) under efficient stirring at room temperature. The precipitate was filtered off, washed twice with 10 mL of water and dried so as to afford 3.84 g of the title compound as a white solid.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customobtaining
  4. customthe complete consumption of the substrate
  5. concentrationconcentrated under reduced pressure to a slurry that
  6. additionwas diluted with 250 mL of water
  7. washwashed with 100 mL of a 1:1 mixture of diethyl ether and ethyl acetate
  8. stirringunder efficient stirring at room temperature
  9. filtrationThe precipitate was filtered off
  10. washwashed twice with 10 mL of water
  11. customdried so as

出典と根拠

ORDレコード
ord-2dd0100a063c48ccb5ac3b9f6b2acc81
出典データセット
uspto-grants-2012_06
特許番号
US08198298B2

反応ノート

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