HCID 13121307, compound → HCID 13121308, compound

HRID 1702459Notes

Reaction equation

HRID 1702459 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][N:6]1[CH:11]=[C:10]([C:12]([O:14]CC)=[O:13])[C:9](=[O:17])[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22](=[O:23])[C:7]1=2)C>Cl>[C:12]([C:10]1[C:9](=[O:17])[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22](=[O:23])[C:7]=2[N:6]([CH2:5][C:4]([OH:24])=[O:3])[CH:11]=1)([OH:14])=[O:13]

Participants

3

Reactant 1

HCID 13121307HCID 13121307, compound

Product 1

HCID 13121308HCID 13121308, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 3-(ethoxycarbonyl)-4,9-dihydro-4,9-dioxo-1H-cyclohepta[b]pyridine-1-acetic acid ethyl ester (2.2 g, described in example 3) in 5% aqueous HCl (v/v, 90 ml) was heated at reflux for 2 hr. The precipitate was collected by filtration and washed with water to give 1.4 g of the title compound; mp>250° C. (after recrystallization from ethanol); nmr (DMSO-d6) δ5.1 (s, 2H), 7.2 (m, 3H), 7.95 (m, 1H), 8.95 (s, 1H); ir (Nujol*) 2850, 1730, 1707, 1640 cm-1 ; uv λ max (MeOH) 344 nm (ε13,030), 235 (19,030); Anal Calcd for C13H9NO6 : C, 56.73% H, 3.30% N, 5.09%; Found: C, 56.76% H, 3.40% N, 5.05%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hr
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-25505eb3ce234296b5f2674324ad5747
Source dataset
uspto-grants-1983_04
Patent number
US04381304

Reaction notes

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