4-Chloroaniline → HCID 57289360, compound

HRID 28670

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+].OC=[C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=[O:21].C([O-])(=O)C.[Na+]>Cl.O.CO>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:9]=[C:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=[O:21])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of 4-chloroaniline (5.6 g, 44 mmol) in concentrated hydrochloric acid (5 mL) was added sodium nitrite (3.0 g, 44 mmol) dissolved in water (10 mL) portionwise over 20 minutes. The mixture was stirred at 0° C. for 30 minutes. In a separate flask, a cool solution of 2-(hydroxymethylene)cyclohexanone (Organic Syntheses, Collective Vol 4, 1963, pg. 536) (5.0 g, 40 mmol) in methanol (30 mL) was treated with a solution of sodium acetate (8.3 g, 101 mmol) in water (25 mL). The mixture was stirred at 0° C. for 20 minutes and the diazonium salt slurry was added. The combined mixture was stirred for 10-15 minutes, collected by filtration, triturated with ethanol, and collected by filtration to give cyclohexane-1,2-dione (4-chlorophenyl)hydrazone (4.6 g, 49% yield) as a yellow solid. 1H-NMR (DMSO-d6): δ 9.93 (s, 1H), 7.29 (m, 4H), 2.55 (m, 2H), 2.40 (m, 2H), 1.84-1.75 (m, 4H).

Workup

stirringThe mixture was stirred at 0° C. for 20 minutes
stirringThe combined mixture was stirred for 10-15 minutes
filtrationcollected by filtration
customtriturated with ethanol
filtrationcollected by filtration

Sources & evidence

ORD record: ord-1d2fae41e866434da2bf685100ac5eb4
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419997B2

Linked notes

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