Hydrochloric Acid → 1-Amino-2-methylindoline hydrochloride

HRID 1284967Notes

Reaction equation

HRID 1284967 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[ClH:11].[N:12]([O-])=O.[Na+].N([O-])=O.C([O-])(=O)C.[NH4+]>CO.O.[Zn]>[ClH:11].[NH2:12][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH:2]1[CH3:1]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 946NitriteHCID 233052-MethylindolineHCID 517165Ammonium Acetate2×HCID 23668193Sodium Nitrite

Product 1

HCID 27376161-Amino-2-methylindoline hydrochloride

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

135.9 g of 2-methylindoline was dissolved in 750 ml of methanol and 100 ml of concentrated hydrochloric acid was added. The solution was cooled to 15° C. and a 33% solution of sodium nitrite in water was added slowly until the presence of excess nitrite was observed. This reaction mixture was stirred for 30 minutes followed by the addition of 100 g of ammonium acetate. The reaction mixture was cooled to 25°-30° C. and 160 g of zinc dust was added over a period of 20 minutes. Then 670 g of ammonium acetate was added in small portions over a period of 40 minutes. The mixture was stirred for about 60 minutes and then extracted four times with a total of 1 liter of toluene. To the combined toluene extract was added 100 ml of concentrated hydrochloric acid and 80 g of ice. The mixture was cooled and filtered to obtain a solid product. The solid product was washed with toluene and then with acetone and dried. The dried product melted at 272°-4° C. and showed one spot at Rf 0.58 on the Analtech Silica Gel plate, mobile phase hexane/ethylacetate/acetic acid - 7/3/1.

Workup

  1. temperatureThe reaction mixture was cooled to 25°-30° C.
  2. stirringThe mixture was stirred for about 60 minutes
  3. extractionextracted four times with a total of 1 liter of toluene
  4. extractionTo the combined toluene extract
  5. additionwas added 100 ml of concentrated hydrochloric acid and 80 g of ice
  6. temperatureThe mixture was cooled
  7. filtrationfiltered
  8. customto obtain a solid product
  9. washThe solid product was washed with toluene
  10. dry with materialwith acetone and dried

Sources & evidence

ORD record
ord-7a12b31c761e4913871a70177185888e
Source dataset
uspto-grants-1986_01
Patent number
US04564677

Reaction notes

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