Hydrochloric Acid → HCID 18705905, compound

HRID 2287841Notes

Reaction equation

HRID 2287841 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH:11]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:12]2)=[CH:8][C:7]=1[C:22]([O:24]C)=O)[CH2:2][CH2:3][CH3:4].[CH3:26][NH:27]C=O.C[O-].[Na+].CO.Cl>CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH:11]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:12]2)=[CH:8][C:7]=1[C:22]([NH:27][CH3:26])=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 31254N-MethylformamideHCID 10942334Sodium MethoxideHCID 18705844HCID 18705844, compound

Product 1

HCID 18705905HCID 18705905, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 6-butoxy-2-(dipropylamino)-2,3-dihydro-1H-indene-5-carboxylate (75, 0.35 g, 1 mmol) and N-methylformamide (0.59 g, 10 mmol) in DMF (10 mL) at 100° C. and 25% was added sodium methoxide in methanol (0.22 mL, 1 mmol) dropwise over a period of 10 min. The resulting mixture is cooled to room temperature and quenched with water (100 mL). The resulting solid was purified by chromatography to give an oil that was converted into the HCl salt and crystallized from EtOAc/MeOH to yield the title compound 82 as a white solid (m.p.129-130° C.).

Workup

  1. customquenched with water (100 mL)
  2. customThe resulting solid was purified by chromatography
  3. customto give an oil that
  4. customcrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-56275ebc168a4f57a384070baae649a6
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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