Isopropanol → HCID 70456982, compound

HRID 483199Notes

Reaction equation

HRID 483199 reaction equation
[Cl:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH2:13]/[C:14](/C)=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].[C:21]([O:27][CH2:28][C:29]([CH3:41])([CH3:40])[CH2:30][N:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32])(=[O:26])[CH2:22][C:23]([CH3:25])=O.[CH3:42]C(O)C>>[CH3:25][C:23]1([CH3:42])[CH:22]([C:21]([O:27][CH2:28][C:29]([CH3:41])([CH3:40])[CH2:30][N:31]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:32])=[O:26])[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=2[N+:10]([O-:12])=[O:11])[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][NH:13]1

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 643918Methyl 3-aminocrotonateHCID 10108340HCID 10108340, compoundHCID 122489723-CHLORO-2-NITROBENZALDEHYDE

Product 1

HCID 70456982HCID 70456982, compound

Procedure

A mixture of 185 mg of 3-chloro-2-nitrobenzaldehyde, 118 mg of methyl 3-aminocrotonate and 292 mg of 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl acetoacetate in 1 ml of 2-propanol was refluxed for 12 hours, and then the solvent was distilled off under reduced pressure. The residue was purified by a method of column chromatography on silica gel to yield 337 mg of the desired compound (132).

Workup

  1. temperaturewas refluxed for 12 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by a method of column chromatography on silica gel

Sources & evidence

ORD record
ord-7c373083ce3d4fbb96d390ffc50abd9a
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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