Acetic Anhydride → HCID 18951359, compound

HRID 1492695Notes

Reaction equation

HRID 1492695 reaction equation
[OH:1][CH:2]1[C:7]2=[CH:8][C:9]3[C:14]([N:6]2[CH2:5][CH2:4][CH:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=[CH:11][CH:10]=3.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([O:1][CH:2]1[C:7]2=[CH:8][C:9]3[C:14]([N:6]2[CH2:5][CH2:4][CH:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=[CH:11][CH:10]=3)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18951360HCID 18951360, compound

Product 1

HCID 18951359HCID 18951359, compoundYield 99,556.297%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 75 g (0.29 mmol) of ethyl 6,7,8,9-tetrahydro-9-hydroxypyrido[1,2-a]indole-8-carboxylate in 1000 ml of pyridine is treated dropwise within 10 minutes with 59.2 g (0.58 mol) of acetic anhydride. The reaction mixture is heated at 50° C. for 24 hours and the solvent is subsequently evaporated. The residue is taken up in a mixture of ethyl acetate and water (2:1, total 750 ml) and the organic phase is washed with 250 ml of water and twice with 100 ml of 1N hydrochloric acid each time, dried over anhydrous sodium sulfate and evaporated to dryness. In this manner, there are obtained 87 g (100%) of ethyl 9-acetoxy-6,7,8,9-tetrahydropyrido[1,2-a]indole-8-carboxylate as a pale yellow solid, m.p. 98°-100° C.

Workup

  1. customthe solvent is subsequently evaporated
  2. additionThe residue is taken up in a mixture of ethyl acetate and water (2:1, total 750 ml)
  3. washthe organic phase is washed with 250 ml of water and twice with 100 ml of 1N hydrochloric acid each time
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f02f56e5cb4d4b4195a5d3ce1c862f72
Source dataset
uspto-grants-1994_12
Patent number
US05374727

Reaction notes

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