Isopropanol → HCID 178526368, compound

HRID 240582Notes

Reaction equation

HRID 240582 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](/[N:15]=[CH:16]\[N:17](C)C)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.ON.CC([OH:26])C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](/[N:15]=[CH:16]\[NH:17][OH:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 443297Hydroxyamine hydrochlorideHCID 178484249HCID 178484249, compound

Product 1

HCID 178526368HCID 178526368, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A 100 mL, single-neck, round-bottomed flask was charged with (Z)-N′-(4-(benzyloxy)pyridin-2-yl)-N,N-dimethylformamidine (7.66 g, 30.0 mmol), hydroxyl amine hydrochloride (2.40 g, 34.5 mmol), propan-2-ol (33.3 ml), and THF (5 ml). The reaction was heated to 50° C. for 7 hours, then concentrated. The residue was titrated with EtOAc/THF and filtered. The filtrate was concentrated and triturated with dichloromethane to provide the product as a white solid.

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customtriturated with dichloromethane

Sources & evidence

ORD record
ord-a01042e7ed7a4209b5511cc4431bbd69
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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