Acetic Acid → Indacaterol acetate

HRID 218342Notes

Reaction equation

HRID 218342 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:6]2)[CH3:2].[C:30]([OH:33])(=[O:32])[CH3:31]>C(O)(C)C>[C:30]([OH:33])(=[O:32])[CH3:31].[CH2:12]([C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[CH2:1][CH3:2])[CH2:6][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:8]2)[CH3:13]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 6918554Indacaterol

Product 1

HCID 24178422Indacaterol acetate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.168 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (5.523 mmoles) and 1.17 g acetic acid (19.48 mmoles) are dissolved in 60 ml isopropanol at 80° C. The clear solution is allowed to cool slowly. Crystallization takes place spontaneously at 35° C. The suspension is stirred for 17 hours at room temperature and then filtered. The filter cake is washed with 10 ml isopropanol and dried at 60° C./ca 10 mbar for 20 hours.

Workup

  1. temperatureto cool slowly
  2. customCrystallization
  3. customspontaneously at 35° C
  4. filtrationfiltered
  5. washThe filter cake is washed with 10 ml isopropanol
  6. customdried at 60° C./ca 10 mbar for 20 hours

Sources & evidence

ORD record
ord-90ace1bb3a8240ecb7f8f830ce8f7466
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

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