Oxalic Acid → HCID 21071597, compound

HRID 1666818Notes

Reaction equation

HRID 1666818 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:7][C:8]([F:23])([F:22])[O:9][C:10]1[CH:21]=[C:20]2[C:13]([NH:14][CH:15]=[C:16]2[CH2:17][CH2:18][NH2:19])=[CH:12][CH:11]=1.CCOCC>CC(C)=O>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:23][C:8]([F:7])([F:22])[O:9][C:10]1[CH:21]=[C:20]2[C:13]([NH:14][CH:15]=[C:16]2[CH2:17][CH2:18][NH2:19])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 210715962-[5-(Trifluoromethoxy)-1H-indol-3-yl]ethan-1-amine

Product 1

HCID 21071597HCID 21071597, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Add oxalic acid (1.3 eq.) in acetone to a solution of 5-trifluoromethoxytryptamine in acetone. Warm and add Et2O to the cloud point and then placed in the freezer overnight to obtain the title compound as a white crystalline solid: 1H NMR (300 MHz, d6-DMSO): 3.02 (m, 4H), 7.06 (m, 1H), 7.39 (m, 1H), 7.45 (d, 1H), 7.55 (m, 1H), 11.30 (bs, 1H). MS (ES+): m/z 245 (M+H)+, 228 (M−NH2)+; (ES−): m/z 243 (M−H); Analysis for C11H11F3N2O: Calcd.: C, 46.7144; H, 3.9203; N, 8.3809. found: C, 46.55; H, 3.62; N, 8.27.

Workup

  1. temperatureWarm
  2. customplaced in the freezer overnight

Sources & evidence

ORD record
ord-55aeed066b854884a38664b70574dceb
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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