HCID 23298443, compound → HCID 23298415, compound

HRID 2393549Notes

Reaction equation

HRID 2393549 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:9]([CH3:22])[CH2:8]2)([O-])=O>C(O)(=O)C.O.[Zn]>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:9]([CH3:22])[CH2:8]2

Participants

4

Reactant 1

HCID 23298443HCID 23298443, compound

Product 1

HCID 23298415HCID 23298415, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

To 5-nitro-2-(methyl)(phenylmethyl)aminoindane hydrochloride (1.08 g, 3.39 mmol) in 85% acetic acid/water was added zinc powder (3.0 g). The mixture was stirred for 1 minute, filtered through celite and concentrated. The concentrate was neutralized with 2N NaOH and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water, dried over magnesium sulfate, and reduced to a syrup. The oil was treated with IPA/HCl, concentrated and used immediately in the next step.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. additionThe oil was treated with IPA/HCl
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f4b2c168c398474eb48658cea5a5f1fb
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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