Ammonia → HCID 69462384, compound

HRID 1297106Notes

Reaction equation

HRID 1297106 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10]C)=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].Br.N>O>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 7148512HCID 7148512, compound

Product 1

HCID 69462384HCID 69462384, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
95 °C

Procedure

To 400 mg (1.55 mmol) of (2-amino-4,5-dimethoxyphenyl)(phenyl)methanone (XXIaa), add dropwise 2.1 ml of HBr 40% by weight in water. Heat at 95° C. for 12 hours. At 0° C. add ammonia to pH=8.9. Add 100 ml H2O and extract three times with 100 ml of CH2Cl2. Dry on MgSO4, evaporate the CH2Cl2 and purify by silica chromatography (AcOEt 1/hexane 4 then 1/1). Yield: 45%. 1H-NMR (CDCl3, 200 MHz): d 3.92 (s, 3H, OCH3), 6.20 (s, 1H Ar), 7.00 (s, 1H Ar), 7.42–7.61 (m, 5H Ar).

Workup

  1. extractionextract three times with 100 ml of CH2Cl2
  2. customDry on MgSO4
  3. customevaporate the CH2Cl2
  4. custompurify by silica chromatography (AcOEt 1/hexane 4

Sources & evidence

ORD record
ord-9f1340f377034ddc9e9a7dd89553a92a
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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