Potassium Bromide → HCID 10831008, compound

HRID 1597056Notes

Reaction equation

HRID 1597056 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[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][CH:4]=[C:3]([CH3:9])[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 253877Potassium BromideHCID 30141382-Amino-m-cresolHCID 10711225HCID 10711225, compound

Product 1

HCID 10831008HCID 10831008, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This material was prepared as a 1:1 mixture of isomers in 35% yield from the above cyanohydrin (707 mg, 3.02 mmol) and 2-amino-m-cresol (409 mg, 3.32 mmol) using the procedure described above for compound 16. An analytical sample was obtained by recrystallization from EtOAc in hexanes (1.3:1 mixture of isomers). mp: 98° C.; IR (KBr) υ 1701, 1690 cm−1; 1H-NMR (400 MHz, CDCl3) δ 7.38-7.20 (m, 7H), 7.15-7.10 (m, 1H), 5.39 and 5.29 (2×d, J=7.9 and 5.4 Hz, 1H), 5.15-4.90 (m, 3H), 4.40 and 4.23 (2×br s, 2H), 2.58 (S, 3H), 1.34 and 1.14 (2×d, J=6.7 and 7.0 Hz, 3H); 13C-NMR (100.6 MHz, CDCl3) δ 164.82, 164.22, 156.28, 156.12, 150.72, 150.65, 139.40, 136.27, 130.61, 130.43, 128.51, 128.40, 128.14, 128.01, 127.91, 125.20, 125.14, 125.04, 124.98, 108.20, 108.13, 71.02, 70.62, 66.96, 66.77, 50.45, 50.27, 17.35, 16.39, 12.24; FAB MS m/z: 341 (MH+); HRMS calcd for C19H21N2O4 (MH+) 341.1501, found: 341.1490; Anal (C19H2ON2O4) C, H, N.

Sources & evidence

ORD record
ord-a0aca8695621459ab3366fe6d17abd5b
Source dataset
uspto-grants-2001_09
Patent number
US06291640B1

Reaction notes

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