Hydrochloric Acid → HCID 59129151, compound

HRID 468436Notes

Reaction equation

HRID 468436 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-63d2dd7cba5042d58135b2f6268e2424
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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