Hydrazine hydrate (1:1) → tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

HRID 2201675Notes

Reaction equation

HRID 2201675 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([O-])=O.O.NN>CO>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59736984tert-Butyl 2-nitro-4-(thiophen-2-yl)phenylcarbamate

Product 1

HCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (2-nitro-4-(thiophen-2-yl)phenyl)carbamate (1.6 g, 4.99 mmol, 1 eq.) in methanol (20 mL) was added hydrazine hydrate (14 mL) and ferric chloride (0.05 g, 0.3 mmol, 0.06 eq.). The resulting mixture was warmed to 60° C. and stirred for 2 h. The reaction was then filtered through Celite, the solids were washed with MeOH. The filtrate was concentrated under reduced pressure. Water was added to the residue and the suspension was stirred for 1 h. The obtained solid was filtered, washed with hexanes then dried to yield tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (1.2 g, 83% yield).

Workup

  1. filtrationThe reaction was then filtered through Celite
  2. washthe solids were washed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. stirringthe suspension was stirred for 1 h
  6. filtrationThe obtained solid was filtered
  7. washwashed with hexanes
  8. customthen dried

Sources & evidence

ORD record
ord-b1dd6203c0494111bebdc1dca5c9e751
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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