Pyridine → 4-Hydroxychlorpropham

HRID 1580525Notes

Reaction equation

HRID 1580525 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.N1C=CC=CC=1.Cl[C:17]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18]>CN(C=O)C>[Cl:9][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[OH:8])[NH:1][C:17](=[O:18])[O:19][CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformate2×HCID 775784-Amino-2-chlorophenol

Product 1

HCID 922624-Hydroxychlorpropham

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-amino-2-chlorophenol (21.45 grams, 0.15 mole) in dry DMF (150 ml.) and pyridine (11.8 grams) is added at 0°C. slowly dropwise with stirring isopropyl chloroformate (16.5 grams, 0.016 mole). After 4 hours at 0° C. to 5°C., a further one gram of isopropyl chloroformate is added. The mixture is stirred at 25°C. for 16 hours, then poured into ice-dilute hydrochloric acid. After 4 hours stirring and scratching, a solid separates out and is filtered off. Crystallization from methanol gives 14.5 grams, 42%, melting point 89°C. to 90°C.

Workup

  1. additionpoured into ice-dilute hydrochloric acid
  2. stirringAfter 4 hours stirring
  3. filtrationa solid separates out and is filtered off
  4. customCrystallization from methanol
  5. customgives 14.5 grams, 42%, melting point 89°C. to 90°C.

Sources & evidence

ORD record
ord-98495b12889d46a7847e6e7f8b10d10e
Source dataset
uspto-grants-1976_01
Patent number
US03933470

Reaction notes

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