Ammonium Acetate → HCID 22046517, compound

HRID 1821793Notes

Reaction equation

HRID 1821793 reaction equation
[N+](C1C=CC(C[CH:9]([O:16][CH:17](CC2C=CC([N+]([O-])=O)=C(OC)C=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=CC=1OC)([O-])=O.[C:40]([O-:43])(=O)C.[NH4+:44]>CO.[Zn]>[CH2:17]([O:16][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:44])=[C:14]([O:43][CH3:40])[CH:15]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 86587623HCID 86587623, compound

Product 1

HCID 22046517HCID 22046517, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-nitro-3-methoxybenzylbenzyl ether (2.2 g, 8.1 mmol) and ammonium acetate (2.46 g, 32 mmol, 4 eq.) in 30 mL MeOH was stirred at 0° C. and 1.3 g (20 mmol, 2.5 eq.) of zinc dust was added in several portions. After 1 h, the reaction mixture was partitioned between 40 mL water and 40 mL ethyl acetate. The organic phase was dried over MgSO4 and concentrated. The residue was used directly in next step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.35 (m, 5H), 6.82 (s, 1H), 6.77 (d, J=6.3 Hz, 1H), 6.67 (d, J=7.8 Hz, 1H), 4.51 (s, 2H), 4.45 (s, 2H), 3.85 (s, 3H), 3.79 (s, 2H). MS ESI-pos, M+1=244.2.

Workup

  1. customthe reaction mixture was partitioned between 40 mL water and 40 mL ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was used directly in next step without further purification

Sources & evidence

ORD record
ord-76c9bfbdbd954c40ba77edfa8c905860
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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