Benzoyl chloride → HCID 59450538, compound

HRID 1948658Notes

Reaction equation

HRID 1948658 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[CH2:15][CH2:14]2.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[CH2:15][CH2:14]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 59450538HCID 59450538, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Benzoyl chloride (126.9 g, 0.900 mol) was added slowly to a stirred mixture of the product of Step A (121 g, 0.818 mol), triethylamine (99.1 g, 0.982 mol) and catalytic amount of DMAP (1 g, 8.18 mmol) in dichloromethane (1 L) at rt under nitrogen. The mixture was stirred overnight and diluted with dichloromethane (1 L). Then the solution was washed with water, hydrochloric acid (0.5 M, 2×1 L), and brine. The organic layer was dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was dried in vacuo to give the compound. 1H-NMR (400 MHz, CDCl3): δ 8.19-8.22 (m, 2H), 7.83 (d, J=8.1 Hz, 1H), 7.65-7.69 (m, 1H), 7.52-7.55 (m, 2H), 7.37 (s, 1H), 7.22 (dd, J=8.1 Hz, J=2.0 Hz, 1H), 3.17-3.20 (m, 2H), 2.73-2.76 (m, 2H) ppm.

Workup

  1. washThen the solution was washed with water, hydrochloric acid (0.5 M, 2×1 L), and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was dried in vacuo
  6. customto give the compound

Sources & evidence

ORD record
ord-1c6d8439d57544c280c7c2910485c98e
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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