3-(p-Tolyl)acrylic acid → HCID 66795846, compound

HRID 500982Notes

Reaction equation

HRID 500982 reaction equation
[NH2:1][C:2]([CH3:37])([CH3:36])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH:20][CH2:21][C@@H:22]([C:24]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]4[C:25]=3[CH:26]=[CH:27][C:28](=[O:35])[NH:29]4)[OH:23])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.[CH3:38][C:39]1[CH:49]=[CH:48][C:42]([CH:43]=[CH:44][C:45]([OH:47])=[O:46])=[CH:41][CH:40]=1>O1CCCC1.O>[CH3:38][C:39]1[CH:49]=[CH:48][C:42]([CH:43]=[CH:44][C:45]([OH:47])=[O:46])=[CH:41][CH:40]=1.[NH2:1][C:2]([CH3:37])([CH3:36])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][NH:20][CH2:21][C@@H:22]([C:24]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]4[C:25]=3[CH:26]=[CH:27][C:28](=[O:35])[NH:29]4)[OH:23])=[CH:16][CH:17]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 158353-(p-Tolyl)acrylic acidHCID 11169365HCID 11169365, compound

Product 1

HCID 66795846HCID 66795846, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[(R)-2-(2-{4-[4-(2-amino-2-methyl-propoxy)-phenylamino]-phenyl}-ethylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one (0.21 g) was dissolved in a mixture of tetrahydrofuran (1.2 mL) and water (1.2 mL). 4-methyl cinnamic acid (0.07 g, predominantly trans) was added to the stirred solution at room temperature and it dissolved. After approximately 10 minutes, crystallisation occurred. The slurry was stirred overnight and filtered. The cake was washed with aqueous Tetrahydrofuran (1:1 THF:water, 2×0.4 mL, 1×0.2 mL) to afford the title compound which was dried overnight under vacuum at 45° C.

Workup

  1. dissolutionit dissolved
  2. customcrystallisation
  3. filtrationfiltered
  4. washThe cake was washed with aqueous Tetrahydrofuran (1:1 THF:water, 2×0.4 mL, 1×0.2 mL)

Sources & evidence

ORD record
ord-aacfc98c036b4247b09e5f92a3023509
Source dataset
uspto-grants-2010_08
Patent number
US07772250B2

Reaction notes

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