Acetic Anhydride → HCID 23373045, compound

HRID 1898997Notes

Reaction equation

HRID 1898997 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:21][CH3:22])[C:18]=2[Cl:20])[NH:13][CH:12]=1>C(O)=O>[CH:1]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:21][CH3:22])[C:18]=2[Cl:20])[NH:13][CH:12]=1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23373069HCID 23373069, compound

Product 1

HCID 23373045HCID 23373045, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a mixture of formic acid (90%, 1.25 ml) and acetic anhydride (2.75 ml) was added 3-(2-aminoethyl)-4-chloro-5-methoxyindole (220 mg, 0.98 mmol), and the solution was stirred for 10 minutes. Removal of volatile components in vacuo at 30° C. left a residue which was partitioned between aqueous sodium bicarbonate and chloroform. The organic phase was separated, dried (Na2SO4) and evaporated to dryness. Purification by chromatography (SiO2 ; C6H14 /CHCl3) gave 3-(2-formylaminoethyl)-4-chloro-5-methoxyindole (176 mg) m.p. 120-121° C.

Workup

  1. customRemoval of volatile components in vacuo at 30° C.
  2. waitleft a residue which
  3. customwas partitioned between aqueous sodium bicarbonate and chloroform
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness
  7. customPurification by chromatography (SiO2 ; C6H14 /CHCl3)

Sources & evidence

ORD record
ord-dfaaf282d9de42d6ad05d95bdafd32a6
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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