2-Amino-3-Hydroxypyridine → HCID 10496440, compound

HRID 1597055Notes

Reaction equation

HRID 1597055 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([O:16][C:17]([NH:19][C@@H:20]([CH3:32])[CH:21]([C:23]1OC2C=CC=CC=2N=1)[OH:22])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[K+].[Br-]>CCOC(C)=O>[CH2:9]([O:16][C:17]([NH:19][C@@H:20]([CH3:32])[CH:21]([C:23]1[O:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[CH:5][CH:6]=2)[OH:22])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 281142-Amino-3-HydroxypyridineHCID 253877Potassium BromideHCID 10711225HCID 10711225, compound

Product 1

HCID 10496440HCID 10496440, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This material was prepared as a 1:1 mixture of isomers in 12% yield from the above cyanohydrin (978 mg, 4.18 mmol) and 2-amino-3-hydroxypyridine (505 mg, 4.60 mmol) using the procedure described above for compound 16. An analytical sample was obtained by recrystallization from EtOAc in hexanes (one isomer). mp: 159-161° C.; IR (KBr) υ 1719, 1699 cm−1; 1H-NMR (400 MHz, DMSO-d6) δ 8.53 (dd, J=4.8, 1.2 Hz, 1H), 8.18 (d, J=7.8 Hz, 1H), 7.44 (dd, J=8.1, 5.1 Hz, 1H), 7.39-7.08 (m, 6H), 6.33 (d, J=6.0 Hz, 1H), 5.00-4.82 (m, 2H), 4.74 (m, 1H), 4.10-4.00 (m, 1H), 1.21 (d, J=6.7 Hz, 3H); 13C-NMR (100.6 MHz, DMSO-d6) δ 169.34, 155.32, 154.73, 146.08, 142.32, 136.99, 128.21, 127.59, 127.37, 120.57, 119.04, 69.99, 64.99, 49.91, 16.31; FAB MS m/z: 328 (MH+); HRMS calcd for C17Hl8N304 (MH+) 328.1297, found: 328.1286; Anal (C17H17N3O4) C, H, N.

Sources & evidence

ORD record
ord-32177b2ffa164aeba74975a069a738c0
Source dataset
uspto-grants-2001_09
Patent number
US06291640B1

Reaction notes

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