Hydrochloric Acid → 5-Amino-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271081Notes

Reaction equation

HRID 2271081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][C:7](=O)[C:6]=2[CH:13]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+].Cl>CO>[NH2:21][CH:7]1[C:6]2[CH:13]=[C:2]([Cl:1])[CH:3]=[C:4]([CH3:14])[C:5]=2[O:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 43472547-Chloro-9-methyl-3,4-dihydro-2H-benzo[b]oxepin-5-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 223917895-Amino-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepineYield 61.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.0 g of 7-chloro-9-methyl-3,4-dihydro-2H-1-benzoxepin-5-one, 50 ml of anhydrous methanol, 10.9 g of ammonium acetate and 0.63 g of sodium cyanoborohydride were stirred for 5 h at 60° C. and then for 2 days at RT. The reaction mixture was then acidified with hydrochloric acid and then concentrated on a rotary evaporator. The residue was taken up in water, and the solution was rendered alkaline with ammonia solution and extracted with EA. After drying and concentrating, the product was purified by chromatography on silica gel using ethyl acetate/methanol 9:1 and 1.3 g of 5-amino-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine were obtained.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. extractionextracted with EA
  3. customAfter drying
  4. concentrationconcentrating
  5. customthe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f5c39af47cb646ce8e7c41d37c4c9f3d
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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