4-Aminophenol → 3-chloro-N-(4-hydroxyphenyl)propanamide

HRID 1014290Notes

Reaction equation

HRID 1014290 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][CH2:10][CH2:11][C:12](Cl)=[O:13]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:9][CH2:10][CH2:11][C:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)=[O:13]

Participants

5

Reactant 2

HCID 4034-AminophenolHCID 693643-Chloropropionyl chloride

Product 1

HCID 30083813-chloro-N-(4-hydroxyphenyl)propanamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
25 °C

Procedure

The solution of 4-aminophenol (250 g, 2.29 mol, 1 equiv) in CH2Cl2(2L) and saturated NaHCO3 (2L) was stirred for 5 min at 25° C., then 3-chloropropanoyl chloride (314 g, 2.52 mol 1.1 equiv) was added dropwise and the reaction was stirred for an additional 3 h at 25° C. The solids were filtered and dried under high vacuum to afford 3-chloro-N-(4-hydroxyphenyl)propanamide was used to the next step directly. (250 g, crude). 1H NMR (400 MHz, DMSO) δ, 2.96-2.99 (m, 2 H), 4.06-4.10 (m, 2 H), 6.88-6.92 (m 2 H), 7.57-7.60 (m, 2 H), 9.38-9.39 (br, 1 H), 10.1 (br, 1 H).

Workup

  1. filtrationThe solids were filtered
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-82bea76f0da948c3b24a800b5772d68c
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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