Hydrochloric Acid → Methanone, (2-aminophenyl)[4-(phenylmethoxy)phenyl]-

HRID 344834Notes

Reaction equation

HRID 344834 reaction equation
CON(C)[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Li]CCCC.Cl>O1CCCC1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[NH2:7])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 110522422-amino-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 10935571Methanone, (2-aminophenyl)[4-(phenylmethoxy)phenyl]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-methoxy-N-methyl anthranilic acid amide prepared as in Example 1(A)(2.00 g, 11.1 mmol) and 4-benzyloxy-bromobenzene (2.92 g, 11.1 mmol) in anhydrous tetrahydrofuran (65 ml) at -78° C. under nitrogen is added, with vigorous stirring, n-BuLi in hexanes (13.8 ml, 1.6M, 22.2 mmol) at 0.60 ml/min. After 20 min, aqueous hydrochloric acid is added (1N, 20 ml), the mixture extracted with ethyl acetate (150 ml), ethyl acetate washed with water, brine, dried over magnesium sulfate, and concentrated. Recrystallization from hexanes gave 4'-benzyloxy-2-aminobenzophenone as yellow crystals; yield: 2.35 g, (70%); m.p. 99°-101° C.

Workup

  1. customat -78° C.
  2. extractionthe mixture extracted with ethyl acetate (150 ml), ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-117daf84d97946babe1347d2abf4bc03
Source dataset
uspto-grants-1991_10
Patent number
US05053543

Reaction notes

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