2,4,6-Trimethylaniline → HCID 66795765, compound

HRID 1944813Notes

Reaction equation

HRID 1944813 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[C:27]=1[NH2:28]>C(O)C>[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]=[N:28][C:27]2[C:29]([CH3:34])=[CH:30][C:31]([CH3:33])=[CH:32][C:26]=2[CH3:25])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 86663391HCID 86663391, compound

Product 1

HCID 66795765HCID 66795765, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.80 g (15.0 mmol) of 6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde and 2.00 g (15.0 mmol) of 2,4,6-trimethylaniline in 50 ml of dry ethanol was refluxed overnight. The resulting mixture was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 5.80 g (88%) of orange oil. Anal. calc. for C30H33N3: C, 82.72; H, 7.64; N, 9.65. Found: C, 82.89; H, 7.73; N, 9.54. 1H NMR (CDCl3): 8.40-8.42 (m, 2H, CH═N and 3-H in Py), 7.99 (m, 1H, 4-H in Py), 7.91 (d, J=8.4 Hz, 1H, 4-H in naphthyl), 7.87 (m, 1H, 8-H in naphthyl), 7.66 (d, J=8.4 Hz, 1H, 3-H in naphthyl), 7.55 (m, 1H, 5-H in Py), 7.36-7.47 (m, 3H, 5,6,7-H in naphthyl), 6.90 (s, 2H, 3,5-H in mesityl), 3.60 (d, J=10.9 Hz, 1H, CHH′N), 3.53 (d, J=10.9 Hz, CHH′N), 3.40 (s, 1H, NH), 2.29 (s, 3H, 4-Me in mesityl), 2.17 (s, 6H, 2,6-Me in mesityl), 0.96 (s, 9H, tBu).

Workup

  1. temperaturewas refluxed overnight
  2. customThe resulting mixture was evaporated to dryness
  3. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.)

Sources & evidence

ORD record
ord-347e29cd70bf496a843c9ae7216fd5dd
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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