Sulfuric Acid → HCID 24178416, compound

HRID 218335Notes

Reaction equation

HRID 218335 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].[S:30](=[O:34])(=[O:33])([OH:32])[OH:31]>C(O)(=O)C>[S:30]([OH:34])([OH:33])(=[O:32])=[O: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 1118Sulfuric AcidHCID 6918554Indacaterol

Product 1

HCID 24178416HCID 24178416, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2.063 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (5.256 mmoles) are dissolved in 12 ml acetic acid at 50° C. A solution of 0.526 g sulfuric acid 98% (5.256 mmoles) in 4 ml acetic acid is adder dropwise, at constant flow rate, over 5 minutes. The clear solution is allowed to cool. Crystallization takes spontaneously place at ca. 35° C. The suspension is stirred for 18 h at room temperature and then filtered. The crystals are washed with 4 ml acetic acid and 10 ml ethylacetate. The salt is dried first for 20 hours at 70° C. and ca. 10 mbar and then for 2 hours at 60° C. and ca. 1 mbar. Yield: 2.31 g white powder (86.9%)

Workup

  1. temperatureto cool
  2. customCrystallization
  3. customtakes spontaneously place at ca. 35° C
  4. filtrationfiltered
  5. washThe crystals are washed with 4 ml acetic acid and 10 ml ethylacetate
  6. customThe salt is dried first for 20 hours at 70° C.
  7. waitca. 10 mbar and then for 2 hours at 60° C.

Sources & evidence

ORD record
ord-758c05fd13024a6384a9230aeabc7f2e
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

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