Hydrochloric Acid → HCID 12041752, compound

HRID 1263623Notes

Reaction equation

HRID 1263623 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=O)[CH:15]=1)=[CH:12][CH:11]=[C:10]([NH:17]CC1C=CC=CC=1)[C:9]=2[N+:25]([O-])=O)=[O:5])[CH3:2].Cl>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([NH2:25])[C:10]([NH2:17])=[CH:11][CH:12]=2)[O:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12041751HCID 12041751, compound

Product 1

HCID 12041752HCID 12041752, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl-7-benzylamino-8-nitro-4-oxo-4H-chromene-2-carboxylate (1.1 g, 3 mmol), Pd/C (0.10 g, 10%), and HCl (12 N 2 mL) in ethanol (90 mL) was hydrogenated for 12 hours. The catalyst was filtered through diatomaceous earth and solvent was removed under vacuum. The residue was dissolved in EtOAc (100 mL) and then washed with saturated NaHCO3 and concentrated to give 684 mg (97%) of product as a thick oil. The product was used without any further purification. 1H NMR (400 MHz), CDCl3) δ1.26 (t, J=7.1 Hz, 3H) 2.19 (m, 2H), 2.70 (m, 1H), 3.18) bs, 4H), 4.22 (q, J=7.1 Hz, 2H), 4.66 (m, 1H), 6.30 (d, J=8 Hz, 1H), 6.40 (d, J=8 Hz,1H).

Workup

  1. filtrationThe catalyst was filtered through diatomaceous earth and solvent
  2. customwas removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed with saturated NaHCO3
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-abfeaf6c4ac74004962da9c3001bc5ea
Source dataset
uspto-grants-2003_04
Patent number
US06541501B2

Reaction notes

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