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Lithium Hydroxide → Trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

HRID 484436
Notes
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Reaction equation

HRID 484436 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([NH:17][C:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[C:5](=C=O)[C@H:6](OC)[NH:7]2.[OH-:27].[Li+].[O:29]1[CH2:33]CCC1>O>[C:33]([C@H:6]1[CH2:5][C@H:4]([NH:17][C:18]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:19])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)([OH:29])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86747046trans-5,7-Dichloro-2-methoxy-carbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

Product 1

HCID 15168526Trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

To a suspension of trans-5,7-dichloro-2-methoxy-carbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline (3.11 g, 7.89 mmol) in a mixture of tetrahydrofuran (100 ml) and water (50 ml) was added aqueous lithium hydroxide (17.4 ml of a 0.5M solution, 8.70 mmol) and the resulting mixture was stirred at room temperture for 3 h. The organic solvent was removed in vacuo and the aqueous residue was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×100 ml). The combined extracts were washed with saturated brine (1×100 ml), dried (MgSO4) and evaporated to give the crude product which was recrystallised from ethyl acetate/petroleum ether 60-80 to give the title compound as colourless crystals (2 crops, 2.65 g) identical in physical properties to example 34 step b.

Workup

  1. customThe organic solvent was removed in vacuo
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined extracts were washed with saturated brine (1×100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give the crude product which
  7. customwas recrystallised from ethyl acetate/petroleum ether 60-80

Sources & evidence

ORD record
ord-e988fd1a59784dc194f8c048ca209ffd
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05231102

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes