1-Naphthaldehyde → HCID 2792506, compound

HRID 1020282Notes

Reaction equation

HRID 1020282 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.C(N(CC)CC)C.[C:14]1([CH:24]=O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.[C:26]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:27][C:28]([CH3:30])=O>C(O)C>[CH3:30][C:28]1[NH:1][C:2]2[N:3]([N:4]=[N:5][N:6]=2)[CH:24]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:27]=1[C:26]([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 4

HCID 61951-NaphthaldehydeHCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 178509299HCID 178509299, compound

Product 1

HCID 2792506HCID 2792506, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-aminotetrazole (0.85 g, 10.0 mmole) and triethylamine (0.25 ml, 1.8 mmole) in hot ethanol (25 ml) was added 1-naphthaldehyde (1.36 ml, 10.0 mmole) followed by ethyl acetoacetate (1.28 ml, 10.0 mmole). The clear solution was heated at reflux for 15 h at which time a white powdery precipitate was observed. The mixture was cooled to room temperature, filtered and washed with ethanol and ethyl ether to provide the desired product (1.88 g, 56%) as a white powder. 1H NMR (400 MHz; CDCl3) d 11.0 (s, 1H); 8.6 (d, 1H, J=8.6 Hz); 7.9 (d, 1H, J=8.2 Hz); 7.82 (d, 1H, J=7.8 Hz); 7.68 (at, 1H, J=7.4 Hz); 7.6-7.54 (m, 2H); 7.45 (dd, 1H, J=7.4, 1.1 Hz); 7.40 (at, 1H, J=7.8 Hz); 3.9 (q, 2H, J=7.0 Hz); 2.75 (s, 3H); 0.8 (t, 3H, J=7.0 Hz). LC MS shows MH+ at 336; M+Na at 358; 2M+H at 671 and 2M+Na at 693.

Workup

  1. temperatureThe clear solution was heated
  2. temperatureat reflux for 15 h at which time a white powdery precipitate
  3. filtrationfiltered
  4. washwashed with ethanol and ethyl ether

Sources & evidence

ORD record
ord-ee152d4a161044a7b62a2e957cdceba3
Source dataset
uspto-grants-2014_05
Patent number
US08716319B2

Reaction notes

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