2,3-Dichlorobenzaldehyde → HCID 13457175, compound

HRID 2290315Notes

Reaction equation

HRID 2290315 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:11]/[C:12](/[CH3:18])=[CH:13]\[C:14]([O:16][CH3:17])=[O:15].[CH3:19][C:20]1[N:21]([CH2:27][CH2:28][O:29][CH2:30][C:31](=O)[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:22]([CH3:26])=[C:23]([CH3:25])[N:24]=1>CO>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:31]([CH2:30][O:29][CH2:28][CH2:27][N:21]2[C:22]([CH3:26])=[C:23]([CH3:25])[N:24]=[C:20]2[CH3:19])=[C:32]1[C:33]([O:35][CH2:36][CH3:37])=[O:34]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 13457163HCID 13457163, compound

Product 1

HCID 13457175HCID 13457175, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,3-dichlorobenzaldehyde (8.75 g), methyl 3-aminocrotonate (5.75 g) and ethyl 4-[2-(2,4,5-trimethyl-1-imidazolyl)ethoxy]acetoacetate (14.1 g) in 50 ml of methanol was stirred at reflux temperature for 5 hours. After evaporation to dryness, the residue was dissolved in 2N hydrochloric acid (200 ml) and washed with diethyl ether (3×100 ml) followed by extraction with methylene chloride (4×150 ml). The combined methylene chloride extracts were washed with saturated aqueous sodium carbonate solution (2×200 ml), dried (Na2CO3), filtered and evaporated to give a beige solid (12.5 g). The crude product was chromatographed on silica (40 g), eluting with ethyl acetate. The appropriate fractions were combined and evaporated and the resultant oil (2.1 g) crystallised from diethyl ether (10 ml) to give the title compound, (1.5 g), m.p. 123°-125° C.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. customAfter evaporation to dryness
  3. dissolutionthe residue was dissolved in 2N hydrochloric acid (200 ml)
  4. washwashed with diethyl ether (3×100 ml)
  5. extractionfollowed by extraction with methylene chloride (4×150 ml)
  6. washThe combined methylene chloride extracts were washed with saturated aqueous sodium carbonate solution (2×200 ml)
  7. dry with materialdried (Na2CO3)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-5d689a857c2a477885e924c00ac8fc3b
Source dataset
uspto-grants-1986_10
Patent number
US04616024

Reaction notes

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