Sulfuric Acid → HCID 178518384, compound

HRID 1983962Notes

Reaction equation

HRID 1983962 reaction equation
[NH2:1][C:2]1[C:11]2[C:6]3=[C:7]([C:12](=[O:16])[NH:13][C:14](=[O:15])[C:5]3=[CH:4][CH:3]=1)[CH:8]=[CH:9][CH:10]=2.[N:17]1[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[N:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[N:1]/[C:2]2[CH:3]=[CH:4][C:5]3[C:14](=[O:15])[NH:13][C:12](=[O:16])[C:7]4[C:6]=3[C:11]=2[CH:10]=[CH:9][CH:8]=4)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 17204-Aminonaphthalene-1,8-dicarboximideHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 178518384HCID 178518384, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

3 g (14.13 mmol) of 4-aminonaphthalene-1,8-dicarboximide and 7.56 g (70.65 mmol) of 4-pyridinecarboxaldehyde in 180 mL of a 2:1 mixture of concentrated sulfuric acid and glacial acetic acid were stirred at 80° C. for 2 hours. The mixture was then poured onto ice and slowly neutralized or adjusted to a slightly alkaline pH (pH=about 8) with NaOH. The resulting precipitate was suction-filtered off, washed with copious amounts of water and then dried under vacuum. Yield: 2.28 g (54% of the theoretical), lustrous yellow powder. 1H-NMR (d6-DMSO/300 MHz): δ=6.46 (s, 1H); 7.52-7.56 (m, 2H, aromatic); 7.20 (d, J=5.7 Hz, 2H, pyridyl); 8.38 (m, 1H, aromatic); 8.65 (d, J=5.7 Hz, 2H, pyridyl), 8.71-8.73 (m, 2H, aromatic); 11.41 (s, 1 H, N—H).

Workup

  1. additionThe mixture was then poured onto ice
  2. filtrationThe resulting precipitate was suction-filtered off
  3. washwashed with copious amounts of water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3e18254415ea49f18bad1eecba78ab78
Source dataset
uspto-grants-2009_06
Patent number
US07544215B2

Reaction notes

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