Sodium Carbonate → 4'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde oxime

HRID 989270Notes

Reaction equation

HRID 989270 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:28][OH:29]>C(O)C>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]=[N:28][OH:29])=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 98139384'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde

Product 1

HCID 734155234'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde oximeYield 33.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 27 (33.7 mg), sodium carbonate (27.6 mg), and hydroxylamine hydrochloride (18 mg) in ethanol (5 mL) was set to reflux for 16 hours. Inorganic solid was filtered out and washed with DCM and acetone. Organic layer was concentrated under reduced pressure to give the titled compound (12 mg) without purification. 1H NMR (400 MHz, CDCI3)δ8.19 (s, 1 H), 7.82-7.69 (m, 8 H), 4.37 (d, J=6.3, 2 H), 3.35 (m, 2 H), 3.10-3.03 (m, 2 H), 2.06-1.94 (m, 2 H), 1.93-1.88 (m, 2 H).

Workup

  1. temperatureto reflux for 16 hours
  2. filtrationInorganic solid was filtered out
  3. washwashed with DCM and acetone
  4. concentrationOrganic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-13ed004ddf744982968e36e7e5a8dc90
Source dataset
uspto-grants-2003_10
Patent number
US06638967B2

Reaction notes

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