3-Chlorobenzaldehyde → HCID 74762714, compound

HRID 1054335Notes

Reaction equation

HRID 1054335 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:33]([CH:35]([CH3:37])[CH3:36])#[C-:34]>CO.O>[Cl:12][C:13]1[CH:14]=[C:15]([C:16]2[N:9]=[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:8][N:7]3[C:34]=2[NH:33][CH:35]([CH3:37])[CH3:36])[CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 150783Isopropyl isocyanideHCID 521998p-Toluenesulfonic acid monohydrateHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 74762714HCID 74762714, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5-(trifluoromethyl)pyridin-2-amine (100 mg, 617 μmol, Eq: 1.00), 3-chlorobenzaldehyde (86.7 mg, 70.2 μl, 617 μmol, Eq: 1.00) and p-toluenesulfonic acid monohydrate (35.2 mg, 185 μmol, Eq: 0.3) were dissolved in MeOH (1.00 mL) and the intensive yellow solution was stirred for 5 min. To this yellow solution was added dropwise 2-isocyanopropane (42.6 mg, 58.2 μL, 617 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 90 min. To the yellow solution was added dropwise water and oil was formed. The water/MeOH was separated from the oil and the yellow oily residue was purified by flash column chromatography (40 g SiO2, hexane/AcOEt 100:0 to 0:100) to yield a yellow solid (178 mg, 78.3%). MS: 354.0 [M+H]+; 1H-NMR (D6-DMSO): δ 8.92 (s, 1H), 8.29 (s, 1H), 8.19 (d, 1H), 7.72 (d, 1H), 7.51 (t, 1H), 7.47-7.36 (m, 2H), 5.13 (d, 1H), 3.26 (m, 1H), 1.08 (d, 6H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 90 min
  2. customoil was formed
  3. customThe water/MeOH was separated from the oil
  4. customthe yellow oily residue was purified by flash column chromatography (40 g SiO2, hexane/AcOEt 100:0 to 0:100)

Sources & evidence

ORD record
ord-d7ac1d61fde844ef9f0a1b9d0477e7c1
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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