Hydrochloric Acid → HCID 18705820, compound

HRID 2287845Notes

Reaction equation

HRID 2287845 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([OH:18])=[C:10]([C:14](OC)=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C([NH2:24])=O.C[O-].[Na+].CO.Cl>CN(C=O)C>[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([OH:18])=[C:10]([C:14]([NH2:24])=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 713FormamideHCID 887MethanolHCID 10942334Sodium MethoxideHCID 19710193HCID 19710193, compound

Product 1

HCID 18705820HCID 18705820, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-(dipropylamino)-2,3-dihydro-6-hydroxy-1H-indene-5-caboxylate (86, 0.93 g, 2.9 mmol) and formamide (1.2 mL, 29 mmol) in DMF (20 mL) at 100° C. was added 25% sodium methoxide in methanol (1.3 mL, 5.8 mmol) dropwise. The mixture stirred for 4 h. The reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer is washed with water, brine dried (MgSO4), filtered and concentrated to give the crude product. Chromatographic purification yielded pure product as an oil that was converted into the HCl salt and crystallized from EtOAc/MeOH to give the title compound 87 as a white solid (m.p. 266-267° C.).

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. washThe organic layer is washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customChromatographic purification
  9. customyielded pure product as an oil that
  10. customcrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-948013d85012479eabe24ad7ffd99c61
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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