Hydroxyamine hydrochloride → 4-heptoxy-N'-hydroxybenzenecarboximidamide

HRID 1775795Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[NH2:18][OH:19]>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:13](=[N:18]/[OH:19])/[NH2:14])=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

Conditions

Temperature: 85 °C

Procedure

Prepared using General Procedure 2: To a stirring solution of 4-(heptyloxy)benzonitrile (1.0 g, 4.6 mmol) in EtOH (15 mL) were added hydroxylamine hydrochloride (0.96 g, 13.8 mmol) and TEA (2.22 g, 23.0 mmol). The reaction was heated to 85° C. for 2 h. The solvent was removed under reduced pressure and the residue was diluted with water (20 mL) and extracted with DCM (3×10 mL). The combined organic layers were concentrated under reduced pressure. The crude material was crystallized from isopropanol (20 mL) to afford 1.05 g (91%) of (Z)-4-(heptyloxy)-N′-hydroxybenzimidamide as a white solid. LCMS-ESI (m/z) calculated for C14H22N2O2: 250.2. found 251.3 [M+H]+, tR=1.70 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 7.59 (d, J=8.6 Hz, 2H), 6.93 (t, J=14.7 Hz, 2H), 5.82-5.48 (m, 2H), 3.97 (t, J=6.5 Hz, 2H), 1.83-1.55 (m, 2H), 1.56-1.05 (m, 8H), 0.87 (t, J=6.7 Hz, 3H). 13C NMR (101 MHz CDCl3) δ 159.19, 150.53, 126.64, 125.55, 113.87, 67.40, 31.21, 28.62, 28.40, 25.44, 22.02, 13.92.

Workup

customPrepared
customThe solvent was removed under reduced pressure
additionthe residue was diluted with water (20 mL)
extractionextracted with DCM (3×10 mL)
concentrationThe combined organic layers were concentrated under reduced pressure
customThe crude material was crystallized from isopropanol (20 mL)

Sources & evidence

ORD record: ord-b53bfeed94a2464ca7e372d6e746a7b0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260427B2

Reaction notes

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