Pyridine → HCID 86605583, compound

HRID 131273Notes

Reaction equation

HRID 131273 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.Cl[C:16]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[O:17].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:22][O:21][CH2:20][CH2:19][O:18][C:16]([N:5]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)[CH2:4][CH2:3][N:2]([CH3:14])[CH3:1])=[O:17]

Participants

7

Reactant 4

HCID 1049PyridineHCID 694002-Methoxyethyl chloroformateHCID 516892Sodium BicarbonateHCID 18948816HCID 18948816, compound

Product 1

HCID 86605583HCID 86605583, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-[[2-(dimethylamino)ethyl]amino]benzaldehyde (300 mg) in methylene chloride (4 mL) is added 2-methoxyethyl chloroformate (234 μL) and thereto is added dropwise pyridine (252 μL) under ice-cooling. The mixture is stirred at 50° C. for 2 days. The reaction mixture is diluted with chloroform (5 mL) and thereto is added a saturated sodium hydrogencarbonate solution (10 mL). After stirring, the organic layer is separated and concentrated. The residue is purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10) to give 4-[N-[(2-methoxyethoxy)carbonyl]-N-[2-(dimethylamino)ethyl]amino]benzaldehyde (290 mg, yield; 63%) as an amorphous powder. MS (APCI) m/z: 294 [M+H]+

Workup

  1. temperaturecooling
  2. stirringAfter stirring
  3. customthe organic layer is separated
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10)

Sources & evidence

ORD record
ord-e799903fc09548ef96dcda08f1876ff3
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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