Sodium Hydroxide → HCID 24760119, compound

HRID 913184Notes

Reaction equation

HRID 913184 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([O:34]CC)=[O:33])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]3=[C:11]([O:28][CH2:29][CH3:30])[C:10]=2[CH2:9]1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([OH:34])=[O:33])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]3=[C:11]([O:28][CH2:29][CH3:30])[C:10]=2[CH2:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58012497HCID 58012497, compound

Product 1

HCID 24760119HCID 24760119, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl (3-chloro-4-{4-(ethyloxy)-1-oxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate (0.041 g, 0.08 mmol) was heated to reflux in a 1:1 mixture of 2N sodium hydroxide:ethanol (10 ml) for 1 hour. The reaction was cooled to room temperature. The ethanol was evaporated and the mixture acidified with HCl (2N). The resulting white solid was collected by filtration, washed with water and dried under vacuum. This was purified by MDAP to give the title compound (0.014 g, 0.03 mmol) as a clear foam. LC/MS: Rt=3.42, [MH]+ 494.

Workup

  1. customThe ethanol was evaporated
  2. filtrationThe resulting white solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. customThis was purified by MDAP

Sources & evidence

ORD record
ord-ac407f2eb1484a40870ab8ec1a968e3e
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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