Carbazole → hydroxylamine-O-sulfonic acid

HRID 2217083Notes

Reaction equation

HRID 2217083 reaction equation
CC(C)([O-])C.[K+].[CH:7]1[C:19]2[NH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.[NH2:20][O:21][S:22]([OH:25])(=[O:24])=[O:23].C[N:27]1CCCC1=O.CC(C)([O-])C.[K+].CN1CCCC1=O>CN1CCCC1=O.CC(C)([O-])C.[K+].CN1CCCC1=O>[NH2:20][O:21][S:22]([OH:25])(=[O:24])=[O:23].[CH:16]1([NH2:27])[C:17]2[C:12]([C:11]3[C:19]([N:18]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:13][CH:14]=[CH:15]1

Participants

8

Reactant 4

HCID 6854CarbazoleHCID 23665647Potassium tert-butoxideHCID 86597979HCID 86597979, compoundHCID 131725956HCID 131725956, compound

Product 2

HCID 76284hydroxylamine-O-sulfonic acidYield 97%HCID 219460661H-carbazol-1-amineYield 85%

Reagents, catalysts & solvents 2

HCID 86597979HCID 86597979, compoundCatalystHCID 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 35.9 g of N-methylpyrrolidinone (NMP) is prepared and chilled to 0–5° C. A second solution is prepared from 20.3 g (19.3 g corrected for 95% purity) of potassium tert-butoxide and 35.3 g of NMP. An amination vessel is charged with 7.0 g (6.7 g corrected for 99% purity) of carbazole, 21.7 g of NMP and an initial charge of 1.3 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 22–30° C. to yield a solution containing an 85% yield of 1H-carbazol-1-amine as determined by HPLC.

Workup

  1. temperaturechilled to 0–5° C
  2. temperaturewhile maintaining a reaction temperature of 22–30° C.
  3. customto yield a solution

Sources & evidence

ORD record
ord-cb3553aae3e34b17817219ea8d28e39c
Source dataset
uspto-grants-2006_09
Patent number
US07112682B2

Reaction notes

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