HCID 13121307, compound → HCID 178525830, compound
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.C([O:27]C(C1C(=O)C2C=C(NC(=O)C)C=CC(=O)C=2NC=1)=O)C.C(OC(=O)CN1C=C(C(OCC)=O)C(=O)C2C=C(Cl)C=CC(=O)C1=2)C>>[C:12]([C:10]1[C:9](=[O:17])[C:8]2[CH:18]=[C:19]([OH:27])[CH:20]=[CH:21][C:22](=[O:23])[C:7]=2[N:6]([CH2:5][C:4]([OH:3])=[O:24])[CH:11]=1)([OH:14])=[O:13]Participants
Procedure
In the same manner, but replacing 3-(ethoxycarbonyl)4,9-dihydro-4,9-dioxo-1H-cyclohepta[b]pyridine-1-acetic acid ethyl ester with an equivalent amount of either 3-(ethoxycarbonyl)-4,9-dihydro-6-(N-methylacetylamino)-4,9-dihydro-1H-cyclohepta[b]pyridine-1-acetic acid ethyl ester, 6-(acetylamino)-4,9-dihydro-4,9-dioxo-1H-cyclohepta[b]pyridine-3-carboxylic acid ethyl ester or 6-chloro-3-(ethoxycarbonyl)-4,9-dihydro-4,9-dioxo-1H-cyclohepta[b]pyridine-1-acetic acid ethyl ester, gave the same product, namely 3-carboxy-4,9-dihydro-6-hydroxy-4,9-dioxo-1H-cyclohepta[b]pyridine-1-acetic acid (I; R1 =COOH and R2 =6-OH); mp>250° C. (after recrytallization from acetone); nmr (DMSO-d6) δ5.5 (s, 2H), 7.5 (d, H), 8.3 (d, 1H),8.9 (s, 1H); ir (Nujol*) 2900, 1743, 1694 cm-1 ; uv λ max (MeOH) 341 nm (ε12,500), 237 (32,000); Anal Calcd for C13H9NO7 : C, 53.62% H, 3.12% N, 4.81%; Found: C, 53.22% H, 3.05% N, 4.73%.
Sources & evidence
- ORD record
- ord-f3bebafcd3b34e0fb2c2186cf4f5e9db
- Source dataset
- uspto-grants-1983_04
- Patent number
- US04381304
Reaction notes
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