Hydrochloric Acid → HCID 68426467, compound

HRID 642422Notes

Reaction equation

HRID 642422 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](Br)[C:9]2[N:10]([CH3:20])[C:11]3[C:16]([C:17]=2[C:18]=1[OH:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[C:22]([Cu])#[N:23].[OH-].[NH4+].Cl>CN1C(=O)CCC1.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:22]#[N:23])[C:9]2[N:10]([CH3:20])[C:11]3[C:16]([C:17]=2[C:18]=1[OH:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86617365HCID 86617365, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68426467HCID 68426467, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-bromo-4-hydroxy-9-methyl-9H-beta-carboline-3-carboxylic acid ethyl ester (256 mg), CuCN (132 mg) in NMP (N-methyl 2-pyrrolidinone, 2 mL) was heated at 120° C. for 67 min. The mixture was poured into a stirring mixture of EtOAc and diluted ammonium hydroxide solution, then acidified with conc. HCl; then the organic phase was separated from aqueous and washed with sat. NaCl solution, dried over anhydrous sodium sulfate, filtered, concentrated; the residue was purified with column to give the desired product (84 mg). The title compound, ESI MS (m/z): 296 (M+H)+.

Workup

  1. customthen the organic phase was separated from aqueous and
  2. washwashed with sat. NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified with column

Sources & evidence

ORD record
ord-8edcad9e16e948eead67505554eba26c
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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