Pyridine → HCID 136334154, compound

HRID 1372141Notes

Reaction equation

HRID 1372141 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl.[NH2:22][OH:23].N1C=CC=CC=1>CO.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]=[N:22][OH:23])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 21071779HCID 21071779, compound

Product 1

HCID 136334154HCID 136334154, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-(3-fluoro-4-hydroxyphenyl)-naphthalene-1-carbaldehyde (570 mg, 2.13 mmol), hydroxylamine hydrochloride (297 mg, 4.27 mmol), and anhydrous pyridine (0.35 ml, 4.27 mmol) in MeOH (13 ml) was heated to reflux for 1.5 h. The mixture was then diluted with ether, washed with water, the organic layer was dried over anhydrous Na2SO4, passed through a silica plug and concentrated. Purification by reverse phase HPLC (water-CH3CN-0.1% TFA) afforded 400 mg (67%) of product as a white solid: mp 187–188° C.; 1H NMR (300 MHz, DMSO-d6): δ 7.12 (2H, m), 7.28 (1H, d, J=11.4 Hz), 7.45 (1H, d, J=7.4 Hz), 7.53–7.64 (2H, m). 7.83 (1H, d, J=7.5 Hz), 7.90 (1H, d, J=7.6), 8.73 (1H, d, J=8.1 Hz), 8.81 (1H, s), 10.08 (1H, s), 11.46 (1H, s); MS m/z 282 ([M+H]+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. washwashed with water
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customPurification by reverse phase HPLC (water-CH3CN-0.1% TFA)

Sources & evidence

ORD record
ord-5da5bd5cb81e4400bf50560aa3a12891
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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