Water → 9-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carboxylic acid

HRID 992557Notes

Reaction equation

HRID 992557 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[OH-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 9908122methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

Product 1

HCID 99074349-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9-(2,5-Dichlorobenzyl)-9H-β-carboline-3-carboxylic acid was prepared as described for the corresponding 9-unsubstituted compound (Hagen et al., Heterocycles 1986, 24:2845). A mixture of methyl 9-(2,5-dichlorobenzyl)-9H-β-carboline-3-carboxylate (15.0 g, 0.0389 mol), sodium hydroxide (2.0 g, 0.05 mol), water (75 mL), and 95% ethanol (200 mL) was refluxed for 1 hour. The mixture was concentrated in vacuo, and the residue dissolved in warm water (500 mL), and the pH adjusted to 3 using dilute HCl with vigorous stirring, resulting in the precipitation of a solid. The fine slurry was filtered, washed thoroughly with water, and dried in vacuo overnight at 70° C., and for another day at 85° C., affording 12.60 g (87%) of product. In another run, the product was isolated in 82% yield after recrystallization from hot acetic acid. The product had the following properties: 1H NMR (300 MHz, DMSO-d6) δ9.16 (s, 1H), 9.08 (s, 1H), 8.59 (d, J=8.0, 1H), 7.60-7.69 (m, 3H), 7.39-7.44 (m, 2H), 6.705 (d, J=2.3, 1H), 5.93 (s, 2H), 1.93 (s, 3H); LRMS calcd for C19H10Cl2N2O2 (M+H) 371, found 371.0.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in warm water (500 mL)
  4. customresulting in the precipitation of a solid
  5. filtrationThe fine slurry was filtered
  6. washwashed thoroughly with water
  7. customdried in vacuo overnight at 70° C.
  8. waitfor another day at 85° C.

Sources & evidence

ORD record
ord-1639b0e2fb4f4fd5b10dce16a922329b
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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