3-Pyridinecarboxaldehyde, 2-amino- → HCID 21103207, compound

HRID 1354803Notes

Reaction equation

HRID 1354803 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][C:20]1[N:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O>CC(O)=O>[C:1]1([C:7]2[C:8]([C:10]3[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=3)=[N:19][C:20]3[C:21]([CH:22]=2)=[CH:24][CH:25]=[CH:26][N:27]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 211032094-(Phenylacetyl)benzoic acid

Product 1

HCID 21103207HCID 21103207, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(Phenylacetyl)benzoic acid (1.0 g, 4.16 mmole) and 2-aminonicotinaldehyde (508 mg, 4.16 mmole) were combined in HOAc (5 mL) in a sealed microwave vessel. The mixture was microwave irradiated to 200° C. internal temperature for 2 hr. The mixture was concentrated. Flash column (5% MeOH/CH2Cl2) gave the title compound as a pale yellow solid (9-1): 1H-NMR (500 MHz, DMSO-d6) δ 13.05 (bs, 1 H), 9.15 (dd, J=1.95, 2.20 Hz, 1 H), 8.58 (m, 2 H), 7.88 (d, J=8.06 Hz, 2 H), 7.71 (m, 1 H), 7.53 (d, J=8.05 Hz, 2 H), 7.36 (m, 3 H), 7.30 (m, 2 H).

Workup

  1. customThe mixture was microwave irradiated to 200° C. internal temperature for 2 hr
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-b18c0640d16f4806a9dd9576325de3fe
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

Loading…