(4-Fluoroanilino)acetic acid → N-(4-fluorophenyl)-N-nitrosoglycine

HRID 1507636Notes

Reaction equation

HRID 1507636 reaction equation
[N:1]([O-:3])=O.[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1>O>[F:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]([N:1]=[O:3])[CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 1133296(4-Fluoroanilino)acetic acidHCID 23668193Sodium Nitrite

Product 1

HCID 86729695N-(4-fluorophenyl)-N-nitrosoglycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium nitrite (3.97 g), 57.5 mmol) in 10 mL water was added to a suspension of N-(4-fluorophenyl)glycine 9.25 g (54.7 mmol) in water (50 mL) under nitrogen. The reaction mixture was stirred until clear, ca. 6 hours. Acidification to pH 3 with HCl precipitated the product which was filtered and washed with water (50 mL) and dried to afford the title product.

Workup

  1. customAcidification to pH 3 with HCl precipitated the product which
  2. filtrationwas filtered
  3. washwashed with water (50 mL)
  4. customdried

Sources & evidence

ORD record
ord-619c6b113ac3433a8679e0371ca4999d
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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