2-Amino-4-methylphenol → HCID 10521103, compound

HRID 1597057Notes

Reaction equation

HRID 1597057 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.[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]=[CH:5][C:4]([CH3:9])=[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 72642-Amino-4-methylphenolHCID 253877Potassium BromideHCID 10711225HCID 10711225, compound

Product 1

HCID 10521103HCID 10521103, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This material was prepared as a 1:1 mixture of isomers in 53% yield from the above cyanohydrin (1.10 g, 4.70 mmol) and 2-amino-p-cresol (636 mg, 5.17 mmol) using the procedure described above for compound 16. An analytical sample was obtained by recrystallization from EtOAc in hexanes (7 : 1 mixture of isomers). mp: 134-135° C.; IR (KBr) υ 1718, 1691 cm−1; 1H-NMR (400 MHz, CDC13) δ 7.47-7.09 (m, 8H), 5.47 (d, J=8.6 Hz, 1H), 5.12-4.87 (m, 4H), 4.54-4.30 (m, 1H), 2.44 (s, 3H), 1.32 and 1.13 (2×d, J=6.7 and 6.7 Hz, 3H); 13C-NMR (100.6 MHz, CDCl3) δ 165.90, 165.19, 156.09, 149.04, 140.24, 136.28, 134.38, 128.34, 128.09, 127.91, 126.32, 119.87, 119.69, 110.23, 70.84, 70.57, 66.92, 66.67, 50.48, 50.29, 21.34, 17.24, 15.32; 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-fb1ff43cf1c64d919b9557844ee4d4e0
Source dataset
uspto-grants-2001_09
Patent number
US06291640B1

Reaction notes

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