2-Aminophenol → HCID 1211386, compound

HRID 1946568Notes

Reaction equation

HRID 1946568 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].CCN(C(C)C)C(C)C>C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])=[O:5]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 1211386HCID 1211386, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-chloronicotinoyl chloride (2.91 g, 16.6 mmol) in ethyl acetate (50 mL) was added to a mixture of 2-aminophenol (2.00 g, 18.3 mmol) and DIPEA (4.8 mL, 27.5 mmol) in ethyl acetate (50 mL) at 4° C. The reaction mixture was stirred for 1 hour. The organic mixture was washed with water and brine then concentrated under reduced pressure. The residue was dissolved in ethanol/THF 1:1 (75 mL) and 15% sodium hydroxide (25 mL) and the mixture was stirred at 50° C. for 45 min. The mixture was cooled down to room temperature and concentrated in vacuo to one third volume and then acidified to pH=2 with 3M HCl. The solid was filtered, washed with water and dried to afford title compound 13 (3.69 g, 81%) as a beige solid. LRMS (ESI): (calc) 248.04 (found) 249.2 (MH)+.

Workup

  1. washThe organic mixture was washed with water and brine
  2. concentrationthen concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol/THF 1:1 (75 mL)
  4. stirring15% sodium hydroxide (25 mL) and the mixture was stirred at 50° C. for 45 min
  5. concentrationconcentrated in vacuo to one third volume
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-e8495d53b3e64159b09e57d816450121
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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