Sodium Nitrite → HCID 178516816, compound

HRID 75200Notes

Reaction equation

HRID 75200 reaction equation
[N:1]([O-:3])=O.[Na+].[N:5]1[C:10]2[NH:11][C:12]3[CH:20]=[N:19][CH: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]=[N:19][CH: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 547591456,11-dihydro-5H-dipyrido[2,3-b:4',3'-f]azepin-5-one

Product 1

HCID 178516816HCID 178516816, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (3.3 g, 0.048 mol) in water (14.4 mL) was added dropwise to a solution of 6,11-dihydro-5H-dipyrido[2,3-b:4′,3′-f]azepin-5-one (4.22 g, 0.02 mol) in acetic acid (80 mL) at room temperature. After the addition was completed, the reaction was stirred for 1.5 hours and 100 mL of water was then added. The mixture was stirred for additional 10 minutes, filtered and dried to give 4.18 g of the desired product. 1H NMR (400 MHz, CD3OD): δ 8.70 (s, 1H), 8.48-8.51 (m, 2H), 8.32 (d, 1H, J=5.2 Hz), 7.56 (d, 1H, J=5.6 Hz), 7.07 (dd, 1H, J1=8 Hz, J2=4.8 Hz). MS [M+H]=241.

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred for additional 10 minutes
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-8dccef25790d4b579a1f414f8fdb1ada
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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