Acetic Anhydride → HCID 350142, compound

HRID 1354859Notes

Reaction equation

HRID 1354859 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:12](OC(=O)C)(=[O:14])[CH3:13].CC1C=CN=C(N)C=1C.C1C[O:31][CH2:30][CH2:29]1>>[C:12]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[O:1][C:30](=[O:31])[CH3:29])(=[O:14])[CH3:13]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 49847212-Amino-5-NitrophenolHCID 110078842-Amino-3,4-dimethylpyridine

Product 1

HCID 350142HCID 350142, compoundYield 90.7%

Procedure

2-Amino-5-nitro-phenol (46) (20 g, 97.3 mmol) was suspended in THF (125 mL) and Acetic-anhydride (75 mL) was added. Di-methyl-amino-pyridine (DMAP) (300 mg, 2.45 mmol) was added and the mixture was stirred for 16 h at room temperature. A solid precipitated and was collected by filtration followed by rinsing with 3:1 hexane/EtOAc (3×100 mL). The solid was dried under high vacuum for 8 h to give the desired product (416) as a yellow powder (21 g, 88.2 mmol, 90.7% yield). LC-MS (ESI): (exact mass: 238.06) m/e=239.2 [M+1]+ (15%), 477.1 [2M+1]+ (100%).

Workup

  1. customA solid precipitated
  2. filtrationwas collected by filtration
  3. washby rinsing with 3:1 hexane/EtOAc (3×100 mL)
  4. customThe solid was dried under high vacuum for 8 h

Sources & evidence

ORD record
ord-2cdd46ffced54505892e888b95fdf05f
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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