Acetic Acid → HCID 69229536, compound

HRID 2224660Notes

Reaction equation

HRID 2224660 reaction equation
[C:1]1(=[O:21])[N:5]([CH2:6][CH2:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12.[N+:22]([CH3:25])([O-:24])=[O:23].C(O)(=O)C.C(N)CCC.C(OC)(OC)OC>CO>[C:4]1(=[O:16])[N:5]([CH2:6][CH2:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=[CH:25][N+:22]([O-:24])=[O:23])[C:1](=[O:21])[C:2]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:3]12

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6375NitromethaneHCID 8007ButylamineHCID 9005Trimethyl orthoformateHCID 114714792-(2'-Phthalimidoethyl) benzaldehyde

Product 1

HCID 69229536HCID 69229536, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

To a stirred suspension of 2-(2′-phthalimidoethyl) benzaldehyde (900 gm, 3.22 mol), in methanol (9.0 Lt) were added nitromethane (521 ml, 9.65 mol), acetic acid (349 ml, 6.1 mol), n-butyl amine (486 ml, 4.72 mol) and trimethyl orthoformate (499 ml, 3 mol) at room temperature. The reaction mixture was then stirred at 30-40° C. for 30 hrs. The greenish coloured solid was filtered at suction, washed with chilled methanol (700 ml) and dried at 50° C. for 8 hrs. This gave the title compound, 649 gm, (62.5%) in the form of cream coloured solid

Workup

  1. filtrationThe greenish coloured solid was filtered at suction
  2. washwashed with chilled methanol (700 ml)
  3. customdried at 50° C. for 8 hrs

Sources & evidence

ORD record
ord-9a13c6774d674f479321677e16a6112a
Source dataset
uspto-grants-2008_05
Patent number
US07378439B2

Reaction notes

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