Sodium borohydride → HCID 21939779, compound

HRID 1242934Notes

Reaction equation

HRID 1242934 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=O)[C:10](=[CH:16][N:17]([CH3:19])[CH3:18])[CH2:9][CH2:8]2)(=O)C.[BH4-].[Na+]>CO>[CH3:19][N:17]([CH2:16][C:10]1[CH2:9][CH2:8][C:7]2[CH:6]=[C:5]([NH2:4])[CH:14]=[CH:13][C:12]=2[CH:11]=1)[CH3:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57373319HCID 57373319, compound

Product 1

HCID 21939779HCID 21939779, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The obtained 6-acetamido-2-(N,N-dimethylaminomethylidene)-1-tetralone (4.50 g, 0.0173 mol) was dissolved in methanol (50 ml), and sodium borohydride (6.56 g, 0.173 mol) was added to the solution under ice-cooling, which was stirred for 2 hours. The reaction mixture was concentrated. Ethyl acetate and sodium hydrogencarbonate solution were added to the residue, and extraction was conducted. The ethyl acetate layer was concentrated, and 30 ml of tetrahydrofuran and 30 ml of 2N hydrochloric acid were added to the residue, which was refluxed with heating for 16 hours. The reaction mixture was concentrated, and ethyl acetate and 2N sodium hydroxide solution were added, and extraction was conducted. The ethyl acetate layer was concentrated, and the residue was refined using alumina column chromatography (development solvent; ethyl acetate:n-hexane=30:70), to give 6-[(N,N-dimethylamino)methyl]-7,8-dihydro-2-naphthaleneamine (1.60 g) as a colorless oily substance.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionEthyl acetate and sodium hydrogencarbonate solution were added to the residue, and extraction
  4. concentrationThe ethyl acetate layer was concentrated
  5. addition30 ml of tetrahydrofuran and 30 ml of 2N hydrochloric acid were added to the residue, which
  6. temperaturewas refluxed
  7. temperaturewith heating for 16 hours
  8. concentrationThe reaction mixture was concentrated
  9. additionethyl acetate and 2N sodium hydroxide solution were added
  10. extractionextraction
  11. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-e34d1536105641398c0fa90fe9213d75
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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