Methylamine → 2-(4-Bromo-phenyl)-N-methyl-isobutyramide

HRID 1453028Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9](O)=[O:10])=[CH:4][CH:3]=1.C(OCC)(=O)CC(O)=O.CN.BrC1C=CC([C@H:32]([NH2:34])C)=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([NH:34][CH3:32])=[O:10])=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6329Methylamine

HCID 70615Monoethyl malonate

HCID 853000(R)-4-bromo-alpha-methylbenzylamine

HCID 109336792-(4-Bromophenyl)-2-methylpropanoic acid

Product 1

HCID 587627572-(4-Bromo-phenyl)-N-methyl-isobutyramideYield 84%

Procedure

The title compound was prepared as described in Step 1 of Example A(39), where 2-(4-bromophenyl)-2-methyl propionic acid was substituted for ethyl hydrogen malonate and methyl amine was substituted instead of (R)-(+)-1-(4-bromophenyl)ethylamine on that example. Yield 84%. 1H NMR (CDCl3) δ: 1.55 (s, 6H), 2.72 (d, J=4.6 Hz, 3H), 5.15 (brs, 1H), 7.22-7.26 (m, 2H), 7.46-7.50 (m, 2H).

Sources & evidence

ORD record: ord-99d1da20fff34224bdfa08ba21aa1259
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473790B2

Reaction notes

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