2-Amino-5-methylphenol → HCID 10783339, compound

HRID 1597058Notes

Reaction equation

HRID 1597058 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].[CH2:10]([O:17][C:18]([NH:20][C@@H:21]([CH3:33])[CH:22]([C:24]1OC2C=CC=CC=2N=1)[OH:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[K+].[Br-]>CCOC(C)=O>[CH2:10]([O:17][C:18]([NH:20][C@@H:21]([CH3:33])[CH:22]([C:24]1[O:8][C:7]2[CH:6]=[C:5]([CH3:9])[CH:4]=[CH:3][C:2]=2[N:1]=1)[OH:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 760822-Amino-5-methylphenolHCID 253877Potassium BromideHCID 10711225HCID 10711225, compound

Product 1

HCID 10783339HCID 10783339, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This material was prepared as a 1:1 mixture of isomers in 71% yield from the above cyanohydrin (1.44 g, 6.15 mmol) and 6-amino-m-cresol (832 mg, 6.77 mmol) using the procedure described above for compound 16. An analytical sample was obtained by recrystallization from EtOAc in hexanes (8:1 mixture of isomers). mp: 108-109° C.; IR (KBr) υ 1692 cm−1; 1H-NMR (400 MHz, CDCl3) δ 7.54 (d, J=8.3 Hz, 1H), 7.36-7.10 (m, 7H), 5.40 and 5.32 (d, J=8.9 and 8.9 Hz, 1H), 5.14-4.85 (m, 3H), 4.42-4.28 (m, 2H), 2.47 (s, 3H), 1.33 and 1.14 (2×d, J=6.7 and 6.7 Hz, 3H); 13C-NMR (100.6 MHz, CDC13) δ 165.08, 156.11, 151.24, 137.95, 136.28, 135.76, 128.52, 128.16, 127.99, 127.90, 125.89, 125.79, 119.38, 119.20, 111.09, 70.99, 70.69, 66.99, 66.76, 50.55, 50.26, 21.70, 17.29, 15.38; FAB MS m/z: 341 (MH+); HRMS calcd for C19H21N2O4 (MH+) 341.1501, found: 341.1490; Anal (C19H20N2O4) C, H, N.

Sources & evidence

ORD record
ord-e9ee2d3123ef497d8f59c1a5c1fa940a
Source dataset
uspto-grants-2001_09
Patent number
US06291640B1

Reaction notes

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