O-(4-Nitrophenyl)hydroxylamine → 1-(4-Hydroxyphenyl)-3-((4-nitrophenoxy)imino)heptan-1-one

HRID 1625195Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][NH2:27])=[CH:22][CH:21]=1)([O-:19])=[O:18]>C(O)(=O)C>[N+:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][N:27]=[C:10]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[O:16])=[CH:24][CH:25]=1)([O-:19])=[O:18]

Participants

Conditions

Temperature: 15 °C

Procedure

1-(4-Hydroxyphenyl)-1,3-heptandione, 1121 g, is dissolved in 4070 g acetic acid. O-(4-Nitrophenyl)hydroxylamine, 784 g, is added in portions keeping the temperature at ca 20° C. The formed slurry is stirred for 3 h, cooled to 15° C., filtered and washed with 1590 g acetic acid. 1944 g wet cake corresponding to 1596 g dry 1-(4-hydroxyphenyl)heptane-1,3-dione-3-[O-(4-nitrophenyl)oxime] is obtained. Yield 88%.

Workup

customat ca 20° C
filtrationfiltered
washwashed with 1590 g acetic acid

Sources & evidence

ORD record: ord-e10c6a8f87024dc3b6dbb10f35e1b4c7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779201B2

Reaction notes

Loading…