Hydrochloric Acid → HCID 15817020, compound

HRID 2395588Notes

Reaction equation

HRID 2395588 reaction equation
[CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[CH:5]([NH2:25])[CH2:4][CH2:3]1.[Li+].[OH-].Cl>C1COCC1.CO.CCOCC.CCOC(C)=O>[CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=3)=[CH:7][C:6]=2[CH:5]([NH2:25])[CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 9798357HCID 9798357, compound2×

Product 1

HCID 15817020HCID 15817020, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

100 mg (0.29 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-aminonaphth-3 -yl)ethynyl]benzoate in a mixture of THF and methanol (Compound 56) was refluxed (2 hours) with 0.5 ml (0.5 mmol) of LiOH (1M aqueous solution). Thereafter the mixture was diluted with Et2O:EtOAc (1:1), and acidified with aqueous HCl to pH5. The organic phase was separated, washed (water and brine), dried (MgSO4) to yield the title compound.

Workup

  1. customThe organic phase was separated
  2. washwashed (water and brine)
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-15a21f2e19f1445db5841fcc31c703be
Source dataset
uspto-grants-1996_02
Patent number
US05489584

Reaction notes

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