Phenylhydrazine → HCID 178470379, compound

HRID 1471811Notes

Reaction equation

HRID 1471811 reaction equation
Cl[C:2]1[C:3]2[C:4](=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:14][CH:15]=2)[N:5]=[CH:6][C:7]=1[C:8]([O:10]CC)=O.C(N(CC)CC)C.[C:28]1([NH:34][NH2:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].[Na+]>C(O)C>[O:10]=[C:8]1[C:7]2[C:2]([C:3]3[C:4](=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:14][CH:15]=3)[NH:5][CH:6]=2)=[N:35][N:34]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 7516PhenylhydrazineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 67281884HCID 67281884, compound

Product 1

HCID 178470379HCID 178470379, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

One equivalent of crude diethyl 4-chloro-6H-pyrrolo[3,4-b]pyridine-3,7-dicarboxylate was dissolved in ethanol (0.2 M) under an atmosphere of nitrogen. Following the addition of 2 equivalents of triethylamine and 1.2 equivalents of phenyl hydrazine, the reaction was heated at 75° C. for 21 hours. After cooling to room temperature a large excess of 1 N NaOH was added and after 5 hours the reaction was concentrated to dryness. 10% HCl (aq.) was added and the brown precipitate was collected by filtration and washed with methylene chloride to afford the product as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35 (br. s., 3H) 4.23-4.52 (m, 2H) 6.96-7.22 (m, 1H) 7.26-7.54 (m, 2H) 7.64-7.89 (m, 1H) 7.99-8.27 (m, 3H) 11.60-11.89 (m, 1H) 13.04-13.29 (m, 1H).

Workup

  1. additionwas added and after 5 hours the reaction
  2. concentrationwas concentrated to dryness
  3. addition10% HCl (aq.) was added
  4. filtrationthe brown precipitate was collected by filtration
  5. washwashed with methylene chloride

Sources & evidence

ORD record
ord-0ee3ad5914be42259847ffbddec3d26e
Source dataset
uspto-grants-2015_04
Patent number
US09012470B2

Reaction notes

Loading…