Water → HCID 21989850, compound

HRID 1528188Notes

Reaction equation

HRID 1528188 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].O.[C:13](OCC)(=[O:15])C>>[N+:8]([C:4]1[C:3]2[O:11][C:13](=[O:15])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 51272912-Amino-6-nitrophenol

Product 1

HCID 21989850HCID 21989850, compoundYield 73%

Procedure

2.27 g of N,N′-carbonyldiimidazole (14 mmol, 1.4 eq) in a homogeneous suspension in 6 ml of ethyl acetate were added to 1.54 g of 2-amino-6-nitrophenol (10 mmol, 1 eq) in solution in 10 ml of ethyl acetate. The reaction medium was vigorously stirred for 3 hours, and then 10 ml of water were added. The stirring was continued for 15 minutes, before evaporating off approximately ¾ of the ethyl acetate. The reaction medium was brought to 0° C. and then 2 ml of 37% hydrochloric acid were added. The stirring was again continued for 15 minutes. The reaction medium was filtered. The solid obtained was washed with a 1 N hydrochloric acid solution, with water and with a water-ethanol (4:1) mixture, and then oven-dried. 1.3 g of product were obtained in the form of a pale yellow solid. Yield=73%.

Workup

  1. waitThe stirring was continued for 15 minutes
  2. custombefore evaporating off approximately ¾ of the ethyl acetate
  3. customwas brought to 0° C.
  4. addition2 ml of 37% hydrochloric acid were added
  5. waitThe stirring was again continued for 15 minutes
  6. filtrationThe reaction medium was filtered
  7. customThe solid obtained
  8. washwas washed with a 1 N hydrochloric acid solution, with water and with a water-ethanol (4:1) mixture
  9. customoven-dried

Sources & evidence

ORD record
ord-e05c8f8323cc4cd7a9153dda5cd58ad5
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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