Hydrochloric Acid → HCID 23118289, compound

HRID 1987769Notes

Reaction equation

HRID 1987769 reaction equation
[N+:1]([C:4]1[C:5]([CH3:30])=[C:6]([CH3:29])[C:7]2[O:11][C:10]([CH2:13][N:14]3[CH2:26][CH2:25][C:24]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[NH:17][C:16]=4[CH2:15]3)([CH3:12])[CH2:9][C:8]=2[C:27]=1[CH3:28])([O-])=O.Cl.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[C:5]([CH3:30])=[C:6]([CH3:29])[C:7]2[O:11][C:10]([CH2:13][N:14]3[CH2:26][CH2:25][C:24]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[NH:17][C:16]=4[CH2:15]3)([CH3:12])[CH2:9][C:8]=2[C:27]=1[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23118287HCID 23118287, compound

Product 1

HCID 23118289HCID 23118289, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.49 g of (±)-2-(5-nitro-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran-2-ylmethyl)-2,3,4,9-tetrahydro-1H-beta-carboline, 2.49 g of stannous chloride, 11 ml of hydrochloric acid and 25 ml of ethanol were added and, after heating at reflux for 6.5 hours, the mixture was poured into ice-water and an aqueous sodium hydroxide solution was added. The reaction solution was extracted with chloroform, washed with saturated saline and dried over anhydrous magnesium sulfate and, after the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=100:3) to obtain 1.07 g of the objective product (melting point: 150-153° C.)

Workup

  1. temperatureafter heating
  2. temperatureat reflux for 6.5 hours
  3. extractionThe reaction solution was extracted with chloroform
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationafter the solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:3)

Sources & evidence

ORD record
ord-f7d3979eed4d475ead3d631b2d2c419c
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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