Hydrazine hydrate (1:1) → 3-phenyl-1H-pyrrole-2-carbohydrazide

HRID 1478398Notes

Reaction equation

HRID 1478398 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][N:9](C(OC(C)(C)C)=O)[C:8]=2[C:19]([O:21]C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:24][NH2:25]>O>[C:1]1([C:7]2[CH:11]=[CH:10][NH:9][C:8]=2[C:19]([NH:24][NH2:25])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 903861371-tert-butyl 2-methyl 3-phenyl-1H-pyrrole-1,2-dicarboxylate

Product 1

HCID 904243233-phenyl-1H-pyrrole-2-carbohydrazideYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-tert-butyl 2-methyl 3-phenyl-1H-pyrrole-1,2-dicarboxylate (7.00 g, 23.0 mmol) in hydrazine monohydrate (30.0 mL, 617 mmol) was heated at 100° C. for 12 h. The reaction mixture was cooled to room temperature and diluted with water (100 mL). The solid precipitated was filtered through a Büchner funnel and dried under reduced to pressure to yield 3-phenyl-1H-pyrrole-2-carbohydrazide (3.80 g, 81.0%) as a white solid. LCMS method B-3: retention time 1.54 min, [M+1]=202.0. 1H NMR (400 MHz, DMSO-d6) δ ppm: 4.32 (s, 2H), 6.23 (d, J=2.8 Hz, 1H), 6.88 (d, J=2.8 Hz, 1H), 7.21-7.26 (m, 1H), 7.32-7.36 (m, 2H), 7.44-7.47 (m, 2H), 8.37 (s, 1H), 11.40 (br s, 1H).

Workup

  1. customThe solid precipitated
  2. filtrationwas filtered through a Büchner funnel
  3. customdried

Sources & evidence

ORD record
ord-6790966cdd214038bf8675e21ae4a6cf
Source dataset
uspto-grants-2016_08
Patent number
US09403834B2

Reaction notes

Loading…