Aluminium lithium hydride → N-[4-(Aminomethyl)-2-chloro-6-methylphenyl]acetamide

HRID 1819682Notes

Reaction equation

HRID 1819682 reaction equation
[C:1]([NH:4][C:5]1[C:12]([CH3:13])=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[Cl:14])(=[O:3])[CH3:2].NC1C(C)=CC(CN)=CC=1Cl.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([NH:4][C:5]1[C:12]([CH3:13])=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][C:6]=1[Cl:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 552557664-(Aminomethyl)-2-chloro-6-methylanilineHCID 58962910N-(2-Chloro-4-cyano-6-methylphenyl)acetamide

Product 1

HCID 58962953N-[4-(Aminomethyl)-2-chloro-6-methylphenyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step G (2): 4-acetamido-3-chloro-5-methylbenzonitrile was reduced to 4-amino-3-chloro-5-methylbenzylamine by heating it at reflux with 2.2 eq. of LAH in THF for 2 hrs. 1H NMR (500 MHz, CD3OD) δ 7.31 (s, 1 H), 7.17 (s, 1 H), 3.73 (s, 2 H), 2.23 (s, 3 H), 2.15 (s, 3 H).

Workup

  1. temperatureby heating it

Sources & evidence

ORD record
ord-ad164ec96c0144ac93b09712038a603f
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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