2-Naphthalenecarboxaldehyde → HCID 2692480, compound

HRID 968852Notes

Reaction equation

HRID 968852 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[CH:20]=O>C(OCC)(=O)C>[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[CH:20]=[N:3][NH:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 62012-NaphthalenecarboxaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 2692480HCID 2692480, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of t-butyl carbazate (7.59 g, 57.4 mmol) in ethyl acetate (22 mL) was added with stirring 2-napthaldehyde (8.98 g, 57.5 mmol). This clear yellow solution was stirred at rt for 15 min. Hexanes (105 mL) was added dropwise and solids precipitated from solution. The slurry was cooled to 0° C., the solids were then filtered and rinsed with cold hexanes (20 mL). A second crop of solids was obtained from the filtrate, filtered and combined with the first crop. The combined solids were recrystallized (EtOAc) and filtered. A second crop was collected by concentrating the filtrate to half its original volume and filtering the resulting solids at 0° C. The two crops of solids were combined and dried in vacuo at 40° C. to afford the title compound as a solid (13.17 g, 85.0%): mp 182.1-190° C. (dec.); 1H NMR (DMSO-d6) δ 11.04 (s, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 7.93-7.86 (m, 4H), 7.52-7.49 (m, 2H), 1.47 (s, 9H); 13C N (DMSO-d6) δ 153.1, 143.9, 134.1, 133.6, 133.1, 129.1, 128.9, 128.5, 128.4, 127.5, 127.3, 123.1, 80.1, 28.8; IR (CHCl3) 3061, 3010, 2982, 1733, 1505, 1369 cm−1; Anal. Calcd. for C16H18N2O2: C, 71.09; H, 6.71; N, 10.36. Found: C, 70.95; H, 6.89; N, 10.31.

Workup

  1. customsolids precipitated from solution
  2. temperatureThe slurry was cooled to 0° C.
  3. filtrationthe solids were then filtered
  4. washrinsed with cold hexanes (20 mL)
  5. customA second crop of solids was obtained from the filtrate
  6. filtrationfiltered
  7. customThe combined solids were recrystallized (EtOAc)
  8. filtrationfiltered
  9. customA second crop was collected
  10. concentrationby concentrating the filtrate to half its original volume
  11. filtrationfiltering the resulting solids at 0° C
  12. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-083b1d44b9f14cd9a5bac9a798575a2d
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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