Methyl Isobutyl Ketone → HCID 19787426, compound

HRID 1657233Notes

Reaction equation

HRID 1657233 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.[CH2:11]([C:15]([CH3:17])=O)[CH:12]([CH3:14])[CH3:13]>C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCCC>[CH3:17][C:15](=[N:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1)[CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 7909Methyl Isobutyl KetoneHCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 19787426HCID 19787426, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

A 50-ml four-neck flask equipped with a Vigreux column (2 cmφ×25 cm) and a dehydrating column (filled with molecular sieve) attached thereon was charged with 5-amino-2-chloro-4-fluorophenol (1 g), methyl isobutyl ketone and heptane (weight ratio, 4:1; 40 g), and p-toluenesulfonic acid (4 mg). The mixture was dehydrated under reflux at 60° C. under reduced pressure (constant at 150 mmHg) for 6 hours. The concentration under reduced pressure gave 1.5 g of 5-(1,3-dimethylbutylidenamino)-2-chloro-4-fluorophenol (yield, 100%), m.p., 92°-97° C.; MS (m/z): 243 (M+) 228, 186; NMR (CDCl3, δ) as a 1:4 mixture of cis and trans forms: 0.80 and 1.00 (d, 6H, J=6 Hz), 1.80 and 2.20 (s, 3H), 2.0-2.2 and 2.35-2.38 (m, 3H), 6.3 and 6.4 (d, 1H, J=7.6 Hz), 6.6-7.0 (broad, 1H), 7.04 (d, 1H, J=9.6 Hz).

Workup

  1. customA 50-ml four-neck flask equipped with a Vigreux column (2 cmφ×25 cm)
  2. additiona dehydrating column (filled with molecular sieve)
  3. concentrationThe concentration under reduced pressure

Sources & evidence

ORD record
ord-33c71a8b17784ff3b2aa1c2499142f15
Source dataset
uspto-grants-1993_10
Patent number
US05256822

Reaction notes

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