Indole → 1-Aminoindole

HRID 2217080Notes

Reaction equation

HRID 2217080 reaction equation
NOS(O)(=O)=O.[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.CC(C)([O-])C.[K+].[NH2:22]OS(O)(=O)=O.N1C2C(=CC=CC=2)C=C1.CN1CCCC1=O.CC(C)([O-])C.[K+].CN1CCCC1=O>CN1CCCC1=O.CC(C)([O-])C.[K+].CN1CCCC1=O>[N:7]1([NH2:22])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1

Participants

8

Reactant 5

HCID 798IndoleHCID 76284hydroxylamine-O-sulfonic acidHCID 23665647Potassium tert-butoxideHCID 86597979HCID 86597979, compoundHCID 131725955HOSA indole NMP

Product 1

HCID 6432211-AminoindoleYield 90.2%

Reagents, catalysts & solvents 2

HCID 86597979HCID 86597979, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

A solution of 33.8 kg (32.8 kg corrected for 97% purity) of hydroxylamine-O-sulfonic acid (HOSA) and 15.8 kg (15.6 kg corrected for 99% purity) of indole in 120.2 kg of N-methylpyrrolidinone (NMP), is prepared and chilled to 0–5° C. A second solution is prepared from 67.0 kg (63.7 kg corrected for 95% purity) of potassium tert-butoxide and 122.6 kg of NMP. An amination vessel is charged with 47.0 kg of NMP and an initial charge of 2.2 kg of the potassium tert-butoxide/NMP solution. The HOSA/indole/NMP solution and the remaining potassium tert-butoxide/NMP solution are then simultaneously and proportionally metered using a metering pumping system consisting of a dual head plunger pump together with coriolis mass flow meters into the amination vessel over a period of 185 minutes while maintaining a reaction temperature of 20–30° C. to yield a solution containing 15.9 kg (90.2% yield) of 1H-indol-1-amine as determined by external standard HPLC assay.

Workup

  1. temperaturechilled to 0–5° C
  2. temperaturewhile maintaining a reaction temperature of 20–30° C.
  3. customto yield a solution

Sources & evidence

ORD record
ord-8f03ef23ba7d46769b959d62f3548a9d
Source dataset
uspto-grants-2006_09
Patent number
US07112682B2

Reaction notes

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