2-Naphthoic acid → HCID 22448917, compound

HRID 2186732Notes

Reaction equation

HRID 2186732 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[C:11]=2[O:10][CH2:9][C:8]1=[O:24])=[N+]=[N-].[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35](O)=[O:36].Cl.CN(C)CCCN=C=NCC>C(O)C.CN(C=O)C.C(OCC)(=O)C.[C].[Pd]>[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35]([NH:1][CH2:4][CH2:5][CH2:6][N:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[C:11]=2[O:10][CH2:9][C:8]1=[O:24])=[O:36]

Participants

8

Reactant 3

HCID 71232-Naphthoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22448996HCID 22448996, compound

Product 1

HCID 22448917HCID 22448917, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3-azidopropyl)-3-oxo-8-(tetrahydropyran-2-yloxy)-3,4-dihydro-2H-1,4-benzoxazine (1.0 g) in ethanol (10 ml) was added to a suspension of 10% palladium carbon (containing 50% water) (100 mg) in ethanol (20 ml), and the mixture was stirred at room temperature for 22 hours under a hydrogen atmosphere. The reaction solution was filtered with Celite, and the solvent was distilled off under reduced pressure to obtain a crude amine. The thus-obtained crude amine was dissolved in DMF (10 ml), and 2-naphthalenecarboxylic acid (780 mg) and 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (865 mg) were added to the resultant solution, and the mixture was stirred at room temperature for 19 hours. The reaction solution was diluted with ethyl acetate, washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=3:2) to obtain the object compound (717 mg, yield 55%).

Workup

  1. filtrationThe reaction solution was filtered with Celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. customto obtain a crude amine
  4. customThe thus-obtained crude amine
  5. stirringthe mixture was stirred at room temperature for 19 hours
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe resultant residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=3:2)

Sources & evidence

ORD record
ord-7e044f980ffa47c5aeac6809646f81f0
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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