3-Chlorobenzaldehyde → HCID 74763783, compound

HRID 1054326Notes

Reaction equation

HRID 1054326 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:30]([CH:32]1[CH2:34][CH2:33]1)#[C-:31]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:31]([NH:30][CH:32]3[CH2:34][CH2:33]3)=[C:13]([C:12]3[CH:15]=[CH:16][CH:17]=[C:10]([Cl:9])[CH:11]=3)[N:8]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 661742-Amino-5-chloropyridineHCID 521998p-Toluenesulfonic acid monohydrateHCID 2758008Isocyanocyclopropane

Product 1

HCID 74763783HCID 74763783, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-chloropyridin-2-amine (100 mg, 778 μmol, Eq: 1.00), 3-chlorobenzaldehyde (115 mg, 93.0 μl, 817 μmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (44.4 mg, 233 μmol, Eq: 0.3) were dissolved in MeOH (1.00 mL) and the intensive yellow solution was stirred for 10 min. To this yellow solution was added dropwise isocyanocyclopropane (52.2 mg, 47.4 μL, 778 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. The solvent was removed and the dark red oil was purified twice by flash column chromatography (ethyl acetate in hexanes) to give the product as yellow solid (45 mg, 18.2%). LC/MS (acid polar): 318.1 [M+H]+; 1H-NMR (CDCl3): δ 8.50 (s, 1H), 8.21 (s, 1H), 8.14 (d, 1H), 7.58 (d, 1H), 7.49 (t, 1H), 7.38 (d, 1H), 7.28 (d, 1H), 5.44 (s, 1H), 2.70 (m, 1H), 0.46-0.39 (m, 4H).

Workup

  1. stirringthe corresponding yellow solution was stirred for 2 h
  2. customThe solvent was removed
  3. customthe dark red oil was purified twice by flash column chromatography (ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d91c3aad364748d1bede9c65528fd0ba
Source dataset
uspto-grants-2016_07
Patent number
US09394304B2

Reaction notes

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