Sodium Nitrite → HCID 178516817, compound

HRID 75209Notes

Reaction equation

HRID 75209 reaction equation
[N:1]([O-:3])=O.[Na+].[N:5]1[C:10]2[NH:11][C:12]3[CH:20]=[CH:19][N:18]=[CH:17][C:13]=3[CH2:14][C:15](=[O:16])[C:9]=2[CH:8]=[CH:7][CH:6]=1>O.C(O)(=O)C>[N:5]1[C:10]2[NH:11][C:12]3[CH:20]=[CH:19][N:18]=[CH:17][C:13]=3[C:14](=[N:1][OH:3])[C:15](=[O:16])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 668868736,11-Dihydro-5H-dipyrido[2,3-b:3',4'-f]azepin-5-one

Product 1

HCID 178516817HCID 178516817, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (0.259 g, 3.75 mmol) in water (1.0 mL) was added dropwise to a solution of 6,11-dihydro-5H-dipyrido[2,3-b:3′,4′-f]azepin-5-one (0.330 g, 1.56 mmol, Intermediate D-6) dissolved in acetic acid (6.0 mL). The mixture was stirred at room temperature for 90 minutes at which time a precipitate had formed. The yellow mixture was reduced to about half original volume in vacuo, and then diluted with 20 mL water and stirred for 30 minutes. A thick precipitate formed which was collected by suction filtration, washed with water and then dried in a vacuum oven at 50° C. overnight. The desired product was obtained as a yellow powder (224 mg, 60%). (2 peaks, ˜2:1 ratio of oxime isomers). 1H NMR (DMSO-d6, ˜2:1 mixture of oxime isomers): δ 12.55 & 12.32 (bs, 1H), 11.41 & 11.18 (bs, 1H), 8.67 (m, 2H), 8.54-8.25 (m, 2H), 7.56 (m, 1H), 7.27 (m, 1H). LC/MS: 241 (M+H)+

Workup

  1. customhad formed
  2. stirringstirred for 30 minutes
  3. customA thick precipitate formed which
  4. filtrationwas collected by suction filtration
  5. washwashed with water
  6. customdried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-68a73b7b1e1b403db5f62b2e54a9048b
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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