Methanol → HCID 12980054, compound

HRID 1797229Notes

Reaction equation

HRID 1797229 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].[CH:11](=O)[CH:12]([CH3:14])[CH3:13].CO>C(O)=O>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[N:4]=[CH:11][CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 6561Isobutyraldehyde2×HCID 69132,4,6-Trimethylaniline

Product 1

HCID 12980054HCID 12980054, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2,4,6-Trimethylaniline (7.0 mL, 50 mmol, Aldrich) was mixed with isobutyraldehyde (4.5 mL, 50 mmol, Aldrich), methanol (20 mL), and formic acid (1 mL of a 88% aqueous solution, Fisher). The reaction mixture became reddish and was stirred at RT for 4 h. Assay by 1H-NMR showed a 2/1 mixture of product/starting materials. Additional isobutyric aldehyde (4 mL, 44 mmol) was added to the reaction mixture and it was stirred for 12 h. At this point assay by 1H-NMR showed a 5/1 mixture of product/amine. The solvent and excess aldehyde was evaporated, the residue was distilled at reduced pressure collecting three fractions: 1. 53–56° C./27 Pa, 1/1 mixture of product/amine; 2. 56–59° C., 7/1 product/amine; 3. 59–60° C., pure product (2.3 g, 24.3%). 1H NMR (CDCl3) 7.52 (d, 1H; J=4.8 Hz); 6.84 (br s, 2H); 2.70 (d of septets, 1H; J=4.8; 6.9 Hz); 2.26 (s, 3H); 2.05 (s, 6H); 1.22 (d, 6H; J=6.9 Hz).

Workup

  1. additiona 2/1 mixture of product/starting materials
  2. stirringwas stirred for 12 h
  3. customThe solvent and excess aldehyde was evaporated
  4. distillationthe residue was distilled at reduced pressure
  5. customcollecting three fractions
  6. addition53–56° C./27 Pa, 1/1 mixture of product/amine
  7. custom56–59° C., 7/1 product/amine
  8. custom59–60° C., pure product (2.3 g, 24.3%)

Sources & evidence

ORD record
ord-2a3a8a179cb54ad4bd4e000cb8343c86
Source dataset
uspto-grants-2006_04
Patent number
US07034093B2

Reaction notes

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