Oxalic Acid → HCID 21071558, compound

HRID 1666817Notes

Reaction equation

HRID 1666817 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[Cl:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:19]=1[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][NH:13]2.CCOC(C)=O.CCOCC>CO>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[Cl:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:19]=1[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][NH:13]2

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 64514011H-Indole-3-ethanamine, 4-chloro-

Product 1

HCID 21071558HCID 21071558, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add dropwise oxalic acid (1.32 g, 1.3 eq.) in MeOH to a solution of 4-chlorotryptamine in EtOAc (2.2 g, 11.3 mmol) with vigorous stirring. When addition was complete, add Et2O to the cloud point and place flask in the freezer to give a solid. Collect the solid by filtration and wash with ether. Dry in a vacuum oven at room temperature to give the title compound as an off-white solid: 1H NMR (300 MHz, d6-DMSO): 3.11 (m, 2H), 3.2 (m, 2H), 7.04 (m, 2H), 7.34 (m, 2H), 11.44 (bs, 1H); MS (ES+): m/z 195 (M+H)+, 178 (M−NH2)+; (ES−): m/z 193 (M−H)−; Analysis for C12H13ClN2O4: Calcd.: C, 50.6263; H, 4.6026; N, 9.8396. found: C, 50.56; H, 4.57; N, 9.66.

Workup

  1. additionWhen addition
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. washwash with ether
  6. customDry in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-188ef535069240feb6e1b2de761c88b9
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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