3,4,5-Trimethoxybenzaldehyde → F1386-0126

HRID 1448950Notes

Reaction equation

HRID 1448950 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[N:15]1([CH2:20][CH2:21][NH2:22])[CH:19]=[CH:18][CH:17]=[CH:16]1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]2[NH:22][CH2:21][CH2:20][N:15]3[CH:19]=[CH:18][CH:17]=[C:16]23)[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 27638162-(1H-pyrrol-1-yl)-1-ethanamine

Product 1

HCID 2770921F1386-0126Yield 62.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,4,5-trimethoxybenzaldehyde (19.6 g) and 2-(1H-pyrrol-1-yl)ethanamine (11 g, described in Example 7) in acetic acid (250 ml) is stirred at room temperature for 48 hr and evaporated under reduced pressure. The residue is partitioned between chloroform and 10% sodium carbonate and the organic phase is separated, washed with water, dried over magnesium sulfate, filtered and evaporated to give 18 g of the title compound, nmr(CDCl3) δ (2.40(s), 3.35(m), 3.84(s), 3.92(m), 5.03(s), 5.65(m), 6.12(t), 6.61(m) and 6.70(s).

Workup

  1. customevaporated under reduced pressure
  2. customThe residue is partitioned between chloroform and 10% sodium carbonate
  3. customthe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-334fae9734624822bb34095114d10e37
Source dataset
uspto-grants-1980_02
Patent number
US04188389

Reaction notes

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