Hydroxyamine hydrochloride → HCID 72557066, compound

HRID 2218638Notes

Reaction equation

HRID 2218638 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:26][OH:27].CCOC(C)=O.CCCCCC>CCO.O>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=[N:26][OH:27])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 21226206Ethyl acetate hexaneHCID 59770421HCID 59770421, compound

Product 1

HCID 72557066HCID 72557066, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Dissolve 2-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-benzaldehyde (110 mg,0.35 mmol) in EtOH (4 mL). In a separate flask, dissolve hydroxylamine hydrochloride (35 mg, 0.5 mmol) in water (1 mL). Add this solution the aldehyde solution and stir at room temperature for 18 h. Pour the reaction into water (300 mL) and extract the product into EtOAc. Dry (MgSO4) and concentrate to give 140 mg crude product. Purity on silica gel using EtOAc/hexane to give 82 mg (72%) title compound as a white solid. 1H NMR (CDCl3) δ 3.31 (br s, 4H), 6.73-7.33 (m, 11H), 7.55 (m, 1H), 7.70 (dd, 1H), 8.58 (s, 1H); MS (ES) 326 (M+1), 324 (M−1). HPLC shows 98% purity.

Workup

  1. additionPour
  2. extractionextract the product into EtOAc
  3. dry with materialDry (MgSO4)
  4. concentrationconcentrate
  5. customto give 140 mg crude product

Sources & evidence

ORD record
ord-ca7fd4940a3d447093561742e7e5a825
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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