Hippuric Acid → HCID 23642183, compound

HRID 218334Notes

Reaction equation

HRID 218334 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:42])(=[O:41])[CH2:31][NH:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>CO>[C:30]([OH:42])(=[O:41])[CH2:31][NH:32][C:33]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:34].[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 464Hippuric AcidHCID 6918554Indacaterol

Product 1

HCID 23642183HCID 23642183, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A suspension of 1.95 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (4.968 mmoles) in 28.5 ml methanol is heated to 45° C. 0.89 g hippuric acid (4.968 mmoles) are added in portions over 5 minutes at 45-50° C. The resulting almost complete solution, is further stirred at 50° C. Spontaneous crystallization occurs after ca 5 minutes. 15 ml methanol are added to the very thick mixture. The suspension is allowed to cool and stirred for 4 hours at room temperature. The suspension is filtered and the salt is washed with 10 ml methanol. The crystals are dried first for 20 hours at 70° C. and ca. 10 mbar and further for 4 hours at 60° C. and ca. 1 mbar. Yield: 2.15 g white powder (75.7%)

Workup

  1. customSpontaneous crystallization
  2. waitoccurs after ca 5 minutes
  3. addition15 ml methanol are added to the very thick mixture
  4. temperatureto cool
  5. stirringstirred for 4 hours at room temperature
  6. filtrationThe suspension is filtered
  7. washthe salt is washed with 10 ml methanol
  8. customThe crystals are dried first for 20 hours at 70° C.

Sources & evidence

ORD record
ord-4d685a8eec29403593335830073a345f
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

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