5-Methoxyindole → hydroxylamine-O-sulfonic acid

HRID 2217082Notes

Reaction equation

HRID 2217082 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2.CC(C)([O-])C.[K+].C[N:25]1CCCC1=O.[NH2:31][O:32][S:33]([OH:36])(=[O:35])=[O:34].CN1CCCC1=O>CN1CCCC1=O>[NH2:31][O:32][S:33]([OH:36])(=[O:35])=[O:34].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([NH2:25])[CH:13]=[CH:12]2

Participants

7

Reactant 4

HCID 138725-MethoxyindoleHCID 23665647Potassium tert-butoxideHCID 86597979HCID 86597979, compound2×HCID 131725956HCID 131725956, compound

Product 2

HCID 76284hydroxylamine-O-sulfonic acidYield 97%HCID 10607077HCID 10607077, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

A solution of 10.0 g (9.7 g corrected for 97% purity) of hydroxylamine-O-sulfonic acid (HOSA) in 33.7 g of N-methylpyrrolidinone (NMP) is prepared and chilled to 0–5° C. A second solution is prepared from 20.1 g (19.1 g corrected for 95% purity) of potassium tert-butoxide and 34.4 g of NMP. An amination vessel is charged with 5.9 g of 5-methoxyindole, 17.8 g of NMP and an initial charge of 0.7 g of the potassium tert-butoxide/NMP solution. The HOSA/NMP solution and the remaining potassium tert-butoxide/NMP solution are then simultaneously and proportionally metered into the amination vessel over a period of 86 minutes while maintaining a reaction temperature of 15–22° C. to yield a solution containing 5.6 g (87% yield) of 5-methoxy-1H-indol-1-amine as determined by internal standard HPLC assay.

Workup

  1. temperaturechilled to 0–5° C
  2. temperaturewhile maintaining a reaction temperature of 15–22° C.
  3. customto yield a solution

Sources & evidence

ORD record
ord-96ed73d651504c439a3efeef408dc499
Source dataset
uspto-grants-2006_09
Patent number
US07112682B2

Reaction notes

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