1-Naphthaldehyde → HCID 19077420, compound

HRID 964712Notes

Reaction equation

HRID 964712 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.B(Cl)(Cl)Cl.[C:18]1([CH:28]=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.[OH-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH:28]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[OH:29])[CH:3]=1

Participants

9

Reactant 5

HCID 61951-NaphthaldehydeHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 11424155(4-Chloro-phenyl)-(neopentyl)-amine

Product 1

HCID 19077420HCID 19077420, compoundYield 67.5%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent3×HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (4-chloro-phenyl)-(neopentyl)-amine (6.58 g, 33.3 mmol) in benzene (15 mL) was added to a solution of boron trichloride (1.0 M in xylenes; 36.6 mL, 36.6 mmol) in benzene (40 mL) at 0° C. under a nitrogen atmosphere. Once the addition was complete, the resulting mixture was heated at reflux for 2 hours and then recooled to 0° C. A solution of 1-naphthaldehyde (5.72 g, 36.6 mmol, 5.0 mL), triethylamine (6.74 g, 66.6 mmol, 9.3 mL) and benzene (15 mL) was then added and the resulting mixture stirred 1 hour before diluting with ethyl acetate and aqueous 2N hydrochloric acid. The resulting mixture was shaken vigorously, the aqueous layer alkalized with aqueous 5N sodium hydroxide, and the layers separated. The aqueous layer was extracted with ethyl acetate (2×). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by flash column chromatography (5:1 hexanes/ethyl acetate) to produce 7.95 g (67%) of the title compound as a pale yellow solid.

Workup

  1. additionOnce the addition
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 2 hours
  4. customrecooled to 0° C
  5. stirringThe resulting mixture was shaken vigorously
  6. customthe layers separated
  7. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. custompurified by flash column chromatography (5:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-02b3888dca4b4edd869ae38b606f252c
Source dataset
uspto-grants-1998_06
Patent number
US05770594

Reaction notes

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