1-Naphthaldehyde → HCID 136088304, compound

HRID 2167315Notes

Reaction equation

HRID 2167315 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.[CH2:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28][C:27]1=O>C(O)C>[C:14]1([CH:24]2[C:31]3[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:35]=4[CH2:34][CH2:33][C:32]=3[NH:1][C:2]3=[N:3][N:4]=[N:5][N:6]23)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 61951-NaphthaldehydeHCID 8471TriethylamineHCID 682662-TetraloneHCID 178509299HCID 178509299, compound

Product 1

HCID 136088304HCID 136088304, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-aminotetrazole (0.850 g, 10.0 mmole) and triethylamine (0.250 ml, 1.8 mmole) in hot ethanol (25 ml) was added 1-naphthaldehyde (1.36 ml, 10.0 mmole) followed by 2-tetralone (1.32 ml, 10.0 mmole). The mixture is refluxed for 72 h after which time a small amount of powdery precipitate is observed. Upon cooling the reaction to room temperature, it was filtered and washed with ethyl ether to provide the desired product (0.189 g, 5.1%) as a tan powder. 1H NMR (400 MHz; DMSO-d6) δ 10.9 (bs, 1H); 9.0 (bs, 1H); 8.05-7.85 (m, 2H); 7.77 (at, 1H, J=7.0 Hz); 7.65 (at, 2H, J=7.0 Hz); 7.42 (at, 1H, J=7.4 Hz); 7.14 (d, 1H, J=7.4 Hz); 7.0-6.75 (m, 3H); 3.0-2.6 (m, 4H). LC MS shows MH+ at 352; 2M+H at 703 and 2M+Na at 725.

Workup

  1. temperatureThe mixture is refluxed for 72 h after which time a small amount of powdery precipitate
  2. temperatureUpon cooling
  3. customthe reaction to room temperature
  4. filtrationit was filtered
  5. washwashed with ethyl ether

Sources & evidence

ORD record
ord-d936de5dd9fb4ba79d5ef5bef00ca042
Source dataset
uspto-grants-2015_06
Patent number
US09045428B2

Reaction notes

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