N,N-Dimethylaniline → HCID 22641405, compound

HRID 2415479Notes

Reaction equation

HRID 2415479 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[CH:14]=[CH:15][NH:16]2)=[CH:11][C:10]=1[CH2:20][CH2:21][CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:26].CN(C)C1C=CC=CC=1>>[ClH:26].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:26])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[CH2:20][CH2:21][CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 22641488HCID 22641488, compound

Product 1

HCID 22641405HCID 22641405, compoundYield 99%

Conditions

Temperature
60 °C

Procedure

A suspension of 900 mg (2.93 mmol) of 7-benzyloxy-6-butyl-1H-quinolin-4-one in 1.44 ml of POCl3 (15.8 mmol) was treated with 0.074 ml of N,N-dimethylaniline and heated at 60° C. for 3 h with stirring. The reaction mixture was then poured into ice water and stirred for 0.5 h. The solid which precipitated was filtered off by suction washed with water and dried in a high vacuum to give 1.05 g (99%) of 7-benzyloxy-6-butyl-4-chloro-quinoline hydrochloride as light gray solid. ISP mass spectrum, m/e: XX (M+1 calculated for C20H20ClNO: 325.84).

Workup

  1. stirringstirred for 0.5 h
  2. customThe solid which precipitated
  3. filtrationwas filtered off by suction
  4. washwashed with water
  5. customdried in a high vacuum

Sources & evidence

ORD record
ord-0ca4dff7a0fc4eeb96e35daa27396c00
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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