Acetic Anhydride → N,5-Dimethyl-1H-indol-2-amine dihydrochloride

HRID 1160156Notes

Reaction equation

HRID 1160156 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[CH2:11]([N:13](CC)[CH2:14]C)[CH3:12].C(OC(=O)C)(=O)C>O.CCOCC>[ClH:1].[ClH:1].[CH3:14][NH:13][C:11]1[NH:9][C:6]2[C:7]([CH:12]=1)=[CH:8][C:3]([CH3:2])=[CH:4][CH:5]=2

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochloride

Product 1

HCID 57435942N,5-Dimethyl-1H-indol-2-amine dihydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

5 g of 1-(4-methylphenyl)hydrazine hydrochloride are dissolved in water and then triethylamine is added until the salt has been neutralized. Extraction is carried out with AcOEt and then the extract is evaporated to dryness. The precipitate formed is dissolved in 30 ml of ether and then a solution of 4.6 ml of acetic anhydride dissolved in 30 ml of ether is added dropwise. The mixture is stirred at 0° C. for 15 minutes and then the precipitate formed is filtered off to produce 3 g of the expected compound.

Workup

  1. extractionExtraction
  2. customthe extract is evaporated to dryness
  3. customThe precipitate formed
  4. additionis added dropwise
  5. customthe precipitate formed
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-a5e4eb59d383489fa7bec22d8e009946
Source dataset
uspto-grants-2010_10
Patent number
US07816368B2

Reaction notes

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