Ammonium Chloride → HCID 86595125, compound

HRID 855946Notes

Reaction equation

HRID 855946 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]([CH3:11])[CH2:7]2.[Cl-:15].[NH4+]>CO.O.[Fe]>[ClH:15].[I:1][C:2]1[CH:3]=[C:4]([NH2:12])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH3:11])=[CH:7]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58936936HCID 58936936, compound

Product 1

HCID 86595125HCID 86595125, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 7-iodo-2-methyl-5-nitro-2,3-dihydro-1H-indole XIV (4.75 g, 0.0156 mol) in methanol (150 mL) at 25° C. was treated with a solution of ammonium chloride (5.22 g, 0.0976 mol) in water (150 mL) and iron powder (3 g, 0.0534 mol). The mixture was heated to 100° C. under a nitrogen atmosphere for 6 h. The reaction mixture was filtered hot through a pad of celite and washed with hot methanol. The filtrate was concentrated in vacuo and the residue partitioned between methylene chloride and water. The layers were separated and the pH of the aqueous layer was adjusted to pH=10 with ammonium hydroxide. The aqueous layer was extracted with methylene chloride and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to a volume of 50 mL. The resulting solution was treated with a 4.0M aqueous hydrochloric acid solution in dioxane and then stirred at 25° C. for 1 h. The precipitate was collected by filtration and washed with methylene chloride and petroleum ether to afford 7-iodo-2-methyl-1H-indol-5-ylamine hydrochloride XV (4.37 g, 81%) as a gray solid: LRMS for freebase C9H11IN2 (M+H)+ at m/z=275.

Workup

  1. filtrationThe reaction mixture was filtered hot through a pad of celite
  2. washwashed with hot methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue partitioned between methylene chloride and water
  5. customThe layers were separated
  6. extractionThe aqueous layer was extracted with methylene chloride
  7. dry with materialthe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a volume of 50 mL
  10. additionThe resulting solution was treated with a 4.0M aqueous hydrochloric acid solution in dioxane
  11. filtrationThe precipitate was collected by filtration
  12. washwashed with methylene chloride and petroleum ether

Sources & evidence

ORD record
ord-339a029f01ab4a59a5d0624666642ab3
Source dataset
uspto-grants-2007_08
Patent number
US07262297B2

Reaction notes

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