Acetic Anhydride → HCID 18405217, compound

HRID 1017733Notes

Reaction equation

HRID 1017733 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]2[O:15][C:16]([CH:18]=O)=[CH:17][C:7]1=2.[Cl-].O[NH3+:26].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:18]([C:16]1[O:15][C:8]2[CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[N:6]([CH2:5][C:4]3[CH:20]=[CH:21][C:22]([Cl:23])=[C:2]([Cl:1])[CH:3]=3)[C:7]=2[CH:17]=1)#[N:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 21645Hydroxylamine HClHCID 18405228HCID 18405228, compound

Product 1

HCID 18405217HCID 18405217, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-(3,4-dichlorobenzyl)-2-formylfuro[3,2-b]pyrrole-5-carboxylate (0.7 g) was dissolved in pyridine (7 mL). To this was added hydroxyammonium chloride (0.23 g) and reaction heated at 90° C. for 30 min. Acetic anhydride (2.5 mL) was added dropwise and reaction heated at 90° C. for a further 2 hours. The reaction was quenched by pouring onto ice/water, and the resulting precipitate was filtered off and dried in vacuo to give a pale brown solid (0.69 g, 100%), NMR d(CDCl3) 3.85 (3H, s), 5.6 (2H, s), 6.85 (2H, d), 6.95 (1H, dd), 7.2 (1H, d), 7.4 (1H, d); M/z (−) 349 (M-H+), 347, 189.

Workup

  1. additionTo this was added
  2. customreaction
  3. temperatureheated at 90° C. for a further 2 hours
  4. customThe reaction was quenched
  5. additionby pouring onto ice/water
  6. filtrationthe resulting precipitate was filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a3b233223f8649909a5c90b9f39ce0cb
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

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