Acetic Anhydride → HCID 21996494, compound

HRID 1978003Notes

Reaction equation

HRID 1978003 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[C:13](OC(=O)C)(=[O:15])C>C(O)=O>[CH:13]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1)=[O:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 21996494HCID 21996494, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

To a solution of 7-amino-1-tetralone (1.70 g, 10.5 mmol) in formic acid (3 ml) was added a mixture of formic acid (8 ml) and acetic anhydride (3 ml), followed by stirring for 10 minutes at room temperature. The reaction mixture was concentrated under reduced pressure. The concentrate was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, which was subjected to extraction with ethyl acetate. The extract solution was washed with brine and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from ethyl acetate/isopropyl ether to give 1.80 g (yield 91%) of the above-titled compound, m.p.137-138° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe extract solution was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-811ae20377ff4461bdfd6b8fbb6260a8
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

Loading…