Methanol → Iron

HRID 616139Notes

Reaction equation

HRID 616139 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]=1[N+:19]([O-])=O)(=[O:3])[CH3:2].CO.[Fe:24]>C(O)(=O)C>[Fe:24].[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]=1[NH2:19])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 23925IronHCID 2658881-Acetamido-4-benzyloxy-2-nitrobenzene

Product 2

HCID 23925IronHCID 203712211-Acetamido-2-amino-4-benzyloxybenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1-Acetamido-4-benzyloxy-2-nitrobenzene is treated with 100 ml. methanol with 1.5 g. iron powder and 1 ml. acetic acid at reflux, followed after one hour with a further addition of 1 ml. of acetic acid and 1.0 g. of iron powder to afford 1-acetamido-2-amino-4-benzyloxybenzene. This latter compound is treated in accordance with the third paragraph of Example I to afford 2-acetamido-5-benzyloxy-1-(3-methoxycarbonyl-2-thioureido)benzene.

Workup

  1. additionfollowed after one hour with a further addition of 1 ml

Sources & evidence

ORD record
ord-bcc108a5a53f45f6b67189af9b0646c0
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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