Hydrochloric Acid → HCID 16772687, compound

HRID 710380Notes

Reaction equation

HRID 710380 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[N+:15]([O-])=O)=[CH:9][CH:8]=1.Cl>CCO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH2:15])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 974573HCID 974573, compound

Product 1

HCID 16772687HCID 16772687, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of Step B (0.29 g; 1.0 mmol), 36% HCl (0.16 ml) and 10% Pd/C (0.17 g) in EtOH (15 ml) was stirred for 3 h at 0° C. under H2 (balloon). The catalyst was removed by filtration through Celite pad, washed with EtOH (2×10 ml) and combined filtrates were evaporated to dryness under reduced pressure and the dark residue was diluted to 10 ml with CH3CN and the white precipitate was filtered off, washed with fresh CH3CN (2 ml) and dried to give the title compound (0.2 g; 70%) as off white solid. 1H-NMR (D2O) (2.86 (tr, 2H, J=7.2 Hz); 3.15 (tr, 2H, J=7.2 Hz); 4.66 (HDO); 5.07 (s, 2H); 6.85-6.89 (m, 3H); 7.02 (m, 1H); 7.11-7.34 (m, 4H).

Workup

  1. customThe catalyst was removed by filtration through Celite pad
  2. washwashed with EtOH (2×10 ml)
  3. customwere evaporated to dryness under reduced pressure
  4. additionthe dark residue was diluted to 10 ml with CH3CN
  5. filtrationthe white precipitate was filtered off
  6. washwashed with fresh CH3CN (2 ml)
  7. customdried

Sources & evidence

ORD record
ord-bcc8b009887342e8b3a0b1c9b848cfd3
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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