Hydrochloric Acid → HCID 59129151, compound

HRID 1847835Notes

Reaction equation

HRID 1847835 reaction equation
[CH3:1][C:2]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=2)([CH3:6])[C:3]([NH2:5])=O.Cl>C1COCC1>[CH3:6][C:2]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=2)([CH3:1])[CH2:3][NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59129191HCID 59129191, compound

Product 1

HCID 59129151HCID 59129151, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-2-(5-nitro-1H-indol-2-yl)propanamide (200 mg, 0.81 mmol) was suspended in THF (5 ml) and cooled to 0° C. Borane-THF complex solution (1.0 M, 2.4 mL, 2.4 mmol) was added slowly and the mixture was allowed to stir overnight at room temperature. The mixture was cooled to 0° C. and carefully acidified with 3 N HCl. THF was evaporated off, water was added and the mixture was washed with ethylacetate. The aqueous layer was made alkaline with 50% NaOH and the mixture was extracted with ethylacetate. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 2-methyl-2-(5-nitro-1H-indol-2-yl)propan-1-amine (82 mg, 43%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customTHF was evaporated off
  3. additionwater was added
  4. washthe mixture was washed with ethylacetate
  5. extractionthe mixture was extracted with ethylacetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6406c32768ce4324b09155b65244ab26
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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