Phenylglyoxal → HCID 23322164, compound

HRID 280318Notes

Reaction equation

HRID 280318 reaction equation
[C:1]1([C:7]([CH:9]=O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[CH2:19][CH:20]([CH3:22])[NH2:21]>>[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[CH2:19][CH:20]([NH:21][CH2:9][CH:7]([OH:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:22]

Participants

3

Reactant 2

HCID 14090PhenylglyoxalHCID 541870α,2,4-Trimethylbenzeneethanamine

Product 1

HCID 23322164HCID 23322164, compound

Procedure

The title compound was prepared in the manner described in Example 9 using phenylglyoxal and 2-(2,4-dimethylphenyl)-1-methylethanamine. The residual oil was chromatographed on Kieselgel 60 using 3% methanol-chloroform. Recrystallization of the resulting solid from hexane gave the title compound m.p. 91-92 as a 6:94 mixture of diastereoisomers. τ(CDCl3) 8.9 (3H, d, J=6 Hz), 7.7 (6H, s), 6.9-7.6 (5H, (m) +2H, disappears with D2O) 5.35 (1H, m), 3.05 (3H, s), 2.68 (5H, m).

Workup

  1. customThe title compound was prepared in the manner
  2. customThe residual oil was chromatographed on Kieselgel 60 using 3% methanol-chloroform
  3. customRecrystallization of the resulting solid from hexane

Sources & evidence

ORD record
ord-33c0f56da80248e6a6139b4be30369e5
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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