Aluminium lithium hydride → N-[4-(Aminomethyl)-2-chloro-6-methylphenyl]acetamide
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
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
- temperatureby heating it
Sources & evidence
- ORD record
- ord-ad164ec96c0144ac93b09712038a603f
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601751B2
Reaction notes
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