Dichloromethane → (5-Aminobiphenyl-3-yl)(morpholin-4-yl)methanone

HRID 530387Notes

Reaction equation

HRID 530387 reaction equation
[N:1]1([C:7]([C:9]2[CH:10]=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H].ClCCl>[Pd].C(OCC)(=O)C.C(O)(=O)C>[NH2:15][C:13]1[CH:14]=[C:9]([C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[O:8])[CH:10]=[C:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:12]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 90041337Morpholin-4-yl(5-nitrobiphenyl-3-yl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 90041595(5-Aminobiphenyl-3-yl)(morpholin-4-yl)methanone

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon (10 wt %, 67.5 mg, 0.063 mmol) was added to a solution of morpholin-4-yl(5-nitrobiphenyl-3-yl)methanone (198 mg, 0.634 mmol) in ethyl acetate (5.7 mL) and acetic acid (0.57 mL). The mixture was fitted with a hydrogen balloon and stirred for 3 hours at room temperature. Dichloromethane was added, and the mixture was filtered through CELITE, rinsed with dichloromethane rinse and washed with saturated aqueous NaHCO3 (30 mL). The organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide (5-aminobiphenyl-3-yl)(morpholin-4-yl)methanone as a white solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.61-7.51 (m, 2H), 7.44 (t, J=7.4 Hz, 2H), 7.37 (dd, J=8.4, 6.2 Hz, 1H), 6.97 (s, 1H), 6.96-6.91 (m, 1H), 6.75-6.63 (m, 1H), 3.89 (s, 2H), 3.85-3.37 (m, 8H).

Workup

  1. filtrationthe mixture was filtered through CELITE
  2. washrinsed with dichloromethane
  3. washrinse
  4. washwashed with saturated aqueous NaHCO3 (30 mL)
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b99fac70cc7a4e579dab1f25686e4ad0
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

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