Acetic Acid → HCID 22105524, compound

HRID 1455987Notes

Reaction equation

HRID 1455987 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH:9]=1)[CH:7]=O.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH2:11]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH2:7][NH:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 225219p-Aminophenylacetic acid ethyl esterHCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 22105524HCID 22105524, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromo-2-benzyloxybenzaldehyde (7.2 g) and ethyl 2-[4-aminophenyl]acetate (4.45 g) were heated on a steam bath for 2 hours. The mixture was cooled and dissolved in ethanol (100 ml) and NaBH4 (0.94 g) was added. The mixture was stirred at ambient temperature for 30 minutes, NaBH4 (0.5 g) added and stirred at ambient temperature for 2 hours. Acetic acid (2 ml) was added dropwise and the solvent evaporated to half volume. The mixture was partitioned between water (100 ml) and diethyl ether (3×75 ml) and the combined organic extracts washed with NaHCO3 (2×50 ml), dried (MgSO4) and evaporated. The residue was subjected to chromatography eluting with CH2Cl2 to give ethyl 2-[4-(2-benzyloxy-5-bromobenzylamino)phenyl]acetate: (yield 6.4 g, m.p. 73° C.).

Workup

  1. temperatureThe mixture was cooled
  2. stirringstirred at ambient temperature for 2 hours
  3. customthe solvent evaporated to half volume
  4. customThe mixture was partitioned between water (100 ml) and diethyl ether (3×75 ml)
  5. washthe combined organic extracts washed with NaHCO3 (2×50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-ba98dbb921a24390a1185187f416b2bc
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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