6-Bromopyridine-2-carbaldehyde → HCID 178442119, compound

HRID 634062Notes

Reaction equation

HRID 634062 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[CH2:10]([CH:12]([C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:16]=1[NH2:17])[CH2:13][CH3:14])[CH3:11]>C(O)C>[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=[N:17]/[C:16]2[C:18]([CH:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[CH:19][CH:20]=[CH:21][C:15]=2[CH:12]([CH2:10][CH3:11])[CH2:13][CH3:14])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 120925482,6-Di(pentan-3-yl)aniline

Product 1

HCID 178442119HCID 178442119, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.00 g (43 mmol) of 6-bromopyridine-2-carbaldehyde, 10.0 g (43 mmol) of 2,6-bis(1-ethylpropyl)aniline in 80 ml of ethanol was refluxed for 8 h. The obtained solution was evaporated to dryness and the residue was re-crystallized from 20 ml of methanol. Yield 11.2 g (65%) of yellow crystalline powder. Anal. calc. for C22H29BrN2: C, 65.83; H, 7.28; N, 6.98. Found: C, 66.01; H, 7.23; N, 6.90. 1H NMR (CDCl3): δ 8.21 (m, 1H, 5-H in Py), 8.15 (s, 1H, CH═N), 7.69 (m, 1H, 4-H in Py), 7.59 (m, 1H, 3-H in Py), 7.10 (m, 1H, 4-H in dipentylphenyl), 7.03-7.04 (m, 2H, 3, 5-H in dipentylphenyl), 2.48 (m, 2H, CHEt2), 1.54 (m, 8H, CH2Me), 0.74 (t, J=7.3 Hz, 12H, CH2Me).

Workup

  1. temperaturewas refluxed for 8 h
  2. customThe obtained solution was evaporated to dryness
  3. customthe residue was re-crystallized from 20 ml of methanol

Sources & evidence

ORD record
ord-33ad3d2f10af4946900c1dfa3ebec12e
Source dataset
uspto-grants-2016_04
Patent number
US09321858B2

Reaction notes

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